4-(2-chloroethyl)thiomorpholine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-amino-6-methoxymethoxy-1,2-benzisoxazole (4.0 g) in N,N-dimethylformamide (DMF) (50 ml) was added sodium hydride (0.74 g) under nitrogen. The reaction was stirred one hour at ambient temperature. A solution of 4-(2-chloroethyl)thiomorpholine (3.6 g) in DMF (25 ml) was added to the reaction and heated to 125° C. for three hours. TLC (5% MeOH/CH2Cl2) revealed the absence of starting material. The reaction was diluted with EtOAc (1 l), washed with brine (4×500 ml), dried (MgSO4), and concentrated in vacuo. Flash column chromatography (silica gel) eluting with 5% acetone/CH2Cl2 afforded the the product (2.0 g). heated to 125° C. for three hours washed with brine (4×500 ml) dried (MgSO4) concentrated in vacuo Flash column chromatography (silica gel) eluting with 5% acetone/CH2Cl2

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-amino-6-methoxymethoxy-1,2-benzisoxazole (4.0 g) in N,N-dimethylformamide (DMF) (50 ml) was added sodium hydride (0.74 g) under nitrogen. The reaction was stirred one hour at ambient temperature. A solution of 4-(2-chloroethyl)thiomorpholine (3.6 g) in DMF (25 ml) was added to the reaction and heated to 125° C. for three hours. TLC (5% MeOH/CH2Cl2) revealed the absence of starting material. The reaction was diluted with EtOAc (1 l), washed with brine (4×500 ml), dried (MgSO4), and concentrated in vacuo. Flash column chromatography (silica gel) eluting with 5% acetone/CH2Cl2 afforded the the product (2.0 g). heated to 125° C. for three hours washed with brine (4×500 ml) dried (MgSO4) concentrated in vacuo Flash column chromatography (silica gel) eluting with 5% acetone/CH2Cl2

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-amino-6-methoxymethoxy-1,2-benzisoxazole (4.0 g) in N,N-dimethylformamide (DMF) (50 ml) was added sodium hydride (0.74 g) under nitrogen. The reaction was stirred one hours at ambient temperature. A solution of 4-(2-chloroethyl)thiomorpholine (3.6 g) in DMF (25 ml) was added to the reaction and heated to 125° C. for three hours. TLC (5% MeOH/CH2Cl2) revealed the absence of starting material. The reaction was diluted with EtOAc (1 l), washed with brine (4×500 ml), dried (MgSO4), and concentrated in vacuo. Flash column chromatography (silica gel) eluting with 5% acetone/CH2Cl2 afforded the the product (2.0 g). heated to 125° C. for three hours washed with brine (4×500 ml) dried (MgSO4) concentrated in vacuo Flash column chromatography (silica gel) eluting with 5% acetone/CH2Cl2

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-amino-6-methoxymethoxy-1,2-benzisoxazole (4.0 g) in N,N-dimethylformamide (DMF) (50 ml) was added sodium hydride (0.74 g) under nitrogen. The reaction was stirred one hour at ambient temperature. A solution of 4-(2-chloroethyl)thiomorpholine (3.6 g) in DMF (25 ml) was added to the reaction and heated to 125° C. for three hours. TLC (5% MeOH/CH2Cl2) revealed the absence of starting material. The reaction was diluted with EtOAc (1 l), washed with brine (4×500 ml), dried (MgSO4), and concentrated in vacuo. Flash column chromatography (silica gel) eluting with 5% acetone/CH2Cl2 afforded the the product (2.0 g). heated to 125° C. for three hours washed with brine (4×500 ml) dried (MgSO4) concentrated in vacuo Flash column chromatography (silica gel) eluting with 5% acetone/CH2Cl2

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-amino-6-methoxymethoxy-1,2-benzisoxazole (4.0 g) in N,N-dimethylformamide (DMF) (50 ml) was added sodium hydride (0.74 g) under nitrogen. The reaction was stirred one hour at ambient temperature. A solution of 4-(2-chloroethyl)thiomorpholine (3.6 g) in DMF (25 ml) was added to the reaction and heated to 125° C. for three hours. TLC (5% MeOH/CH2Cl2) revealed the absence of starting material. The reaction was diluted with EtOAc (1 l), washed with brine (4×500 ml), dried (MgSO4), and concentrated in vacuo. Flash column chromatography (silica gel) eluting with 5% acetone/CH2Cl2 afforded the the product (2.0 g). heated to 125° C. for three hours washed with brine (4×500 ml) dried (MgSO4) concentrated in vacuo Flash column chromatography (silica gel) eluting with 5% acetone/CH2Cl2

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-amino-6-methoxymethoxy-1,2-benzisoxazole (4.0 g) in N,N-dimethylformamide (DMF) (50 ml) was added sodium hydride (0.74 g) under nitrogen. The reaction was stirred one hour at ambient temperature. A solution of 4-(2-chloroethyl)thiomorpholine (3.6 g) in DMF (25 ml) was added to the reaction and heated to 125° C. for three hours. TLC (5% MeOH/CH2Cl2) revealed the absence of starting material. The reaction was diluted with EtOAc (1 l), washed with brine (4×500 ml), dried (MgSO4), and concentrated in vacuo. Flash column chromatography (silica gel) eluting with 5% acetone/CH2Cl2 afforded the the product (2.0 g). heated to 125° C. for three hours washed with brine (4×500 ml) dried (MgSO4) concentrated in vacuo Flash column chromatography (silica gel) eluting with 5% acetone/CH2Cl2

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-amino-6-methoxymethoxy-1,2-benzisoxazole (4.0 g) in N,N-dimethylformamide (DMF) (50 ml) was added sodium hydride (0.74 g) under nitrogen. The reaction was stirred one hour at ambient temperature. A solution of 4-(2-chloroethyl)thiomorpholine (3.6 g) in DMF (25 ml) was added to the reaction and heated to 125° C. for three hours. TLC (5% MeOH/CH2Cl2) revealed the absence of starting material. The reaction was diluted with EtOAc (1 l), washed with brine (4×500 ml), dried (MgSO4), and concentrated in vacuo. Flash column chromatography (silica gel) eluting with 5% acetone/CH2Cl2 afforded the the product (2.0 g). heated to 125° C. for three hours washed with brine (4×500 ml) dried (MgSO4) concentrated in vacuo Flash column chromatography (silica gel) eluting with 5% acetone/CH2Cl2

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-amino-6-methoxymethoxy-1,2-benzisoxazole (4.0 g) in N,N-dimethylformamide (DMF) (50 ml) was added sodium hydride (0.74 g) under nitrogen. The reaction was stirred one hours at ambient temperature. A solution of 4-(2-chloroethyl)thiomorpholine (3.6 g) in DMF (25 ml) was added to the reaction and heated to 125° C. for three hours. TLC (5% MeOH/CH2Cl2) revealed the absence of starting material. The reaction was diluted with EtOAc (1 l), washed with brine (4×500 ml), dried (MgSO4), and concentrated in vacuo. Flash column chromatography (silica gel) eluting with 5% acetone/CH2Cl2 afforded the the product (2.0 g). heated to 125° C. for three hours washed with brine (4×500 ml) dried (MgSO4) concentrated in vacuo Flash column chromatography (silica gel) eluting with 5% acetone/CH2Cl2

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-amino-6-methoxymethoxy-1,2-benzisoxazole (4.0 g) in N,N-dimethylformamide (DMF) (50 ml) was added sodium hydride (0.74 g) under nitrogen. The reaction was stirred one hour at ambient temperature. A solution of 4-(2-chloroethyl)thiomorpholine (3.6 g) in DMF (25 ml) was added to the reaction and heated to 125° C. for three hours. TLC (5% MeOH/CH2Cl2) revealed the absence of starting material. The reaction was diluted with EtOAc (1 l), washed with brine (4×500 ml), dried (MgSO4), and concentrated in vacuo. Flash column chromatography (silica gel) eluting with 5% acetone/CH2Cl2 afforded the the product (2.0 g). heated to 125° C. for three hours washed with brine (4×500 ml) dried (MgSO4) concentrated in vacuo Flash column chromatography (silica gel) eluting with 5% acetone/CH2Cl2