2-hydroxy-N-methylacetamide

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 4.6g (0.0325 mole) of boron trifluoride etherate was added to a solution containing 4.6g (0.025 mole) of (4-chloro-2-methylphenoxy)acetaldehyde and 2.5g (0.028 mole) of N-methylglycolamide in 40 ml of tetrahydrofuran. After 24 hours at ambient temperature, the reaction mixture was concentrated under reduced pressure, extracted with ether, washed with water and dried. Purification by silica chromatography gave 0.7g of 2-(4-chloro-2-methylphenoxymethyl)-3-methyl-4-oxazolidinone as a light yellow oil. the reaction mixture was concentrated under reduced pressure extracted with ether washed with water dried Purification by silica chromatography

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

Procedure: 4.6 g (0.0325 mole) of boron trifluoride etherate was added to a solution containing 4.6 g (0.025 mole) of (4-chloro-2-methylphenoxy)acetaldehyde and 2.5 g (0.028 mole) of N-methylglycolamide in 40 ml of tetrahydrofuran. After 24 hours at ambient temperature, the reaction mixture was concentrated under reduced pressure, extracted with ether, washed with water and dried. Purification by silica chromatography gave 0.7 g of 2-(4-chloro-2-methylphenoxymethyl)-3-methyl-4-oxazolidinone as a light yellow oil. the reaction mixture was concentrated under reduced pressure extracted with ether washed with water dried Purification by silica chromatography

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

Procedure: A suspension of 2.62 g (29.4 mmol) of 2-hydroxy-N-methylacetamide and 16.5 g (58.7 mmol) of supported diisopropylethylamine (Ps-DIEA from Argonaut, loading=3.56 mmol/g) in 250 ml of dichloromethane is admixed in small portions and at ambient temperature with 5.93 g (29.4 mmol) of 4-nitrophenyl chloroformate. Orbital stirring is continued at ambient temperature for 16 hours. The resin is filtered off and rinsed with 150 ml of dichloromethane and the filtrate is concentrated under reduced pressure. This gives 6 g of product in the form or a light yellow solid, which is used as it is in the following step. The resin is filtered off rinsed with 150 ml of dichloromethane the filtrate is concentrated under reduced pressure

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

Procedure: 4.6 g (0.0325 mole) of boron trifluoride etherate was added to a solution containing 4.6 g (0.025 mole) of (4-chloro-2-methylphenoxy)acetaldehyde and 2.5 g (0.028 mole) of N-methylglycolamide in 40 ml of tetrahydrofuran. After 24 hours at ambient temperature, the reaction mixture was concentrated under reduced pressure, extracted with ether, washed with water and dried. Purification by silica chromatography gave 0.7 g of 2-(4-chloro-2-methylphenoxymethyl)-3-methyl-4-oxazolidinone as a light yellow oil. the reaction mixture was concentrated under reduced pressure extracted with ether washed with water dried Purification by silica chromatography

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

Procedure: 4.6g (0.0325 mole) of boron trifluoride etherate was added to a solution containing 4.6g (0.025 mole) of (4-chloro-2-methylphenoxy)acetaldehyde and 2.5g (0.028 mole) of N-methylglycolamide in 40 ml of tetrahydrofuran. After 24 hours at ambient temperature, the reaction mixture was concentrated under reduced pressure, extracted with ether, washed with water and dried. Purification by silica chromatography gave 0.7g of 2-(4-chloro-2-methylphenoxymethyl)-3-methyl-4-oxazolidinone as a light yellow oil. the reaction mixture was concentrated under reduced pressure extracted with ether washed with water dried Purification by silica chromatography

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

Procedure: 4.6 g (0.0325 mole) of boron trifluoride etherate was added to a solution containing 4.6 g (0.025 mole) of (4-chloro-2-methylphenoxy)acetaldehyde and 2.5 g (0.028 mole) of N-methylglycolamide in 40 ml of tetrahydrofuran. After 24 hours at ambient temperature, the reaction mixture was concentrated under reduced pressure, extracted with ether, washed with water and dried. Purification by silica chromatography gave 0.7 g of 2-(4-chloro-2-methylphenoxymethyl)-3-methyl-4-oxazolidinone as a light yellow oil. the reaction mixture was concentrated under reduced pressure extracted with ether washed with water dried Purification by silica chromatography

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

Procedure: 4.6 g (0.0325 mole) of boron trifluoride etherate was added to a solution containing 4.6 g (0.025 mole) of (4-chloro-2-methylphenoxy)acetaldehyde and 2.5 g (0.028 mole) of N-methylglycolamide in 40 ml of tetrahydrofuran. After 24 hours at ambient temperature, the reaction mixture was concentrated under reduced pressure, extracted with ether, washed with water and dried. Purification by silica chromatography gave 0.7 g of 2-(4-chloro-2-methylphenoxymethyl)-3-methyl-4-oxazolidinone as a light yellow oil. the reaction mixture was concentrated under reduced pressure extracted with ether washed with water dried Purification by silica chromatography

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: The compound of Example 84 was manufactured by the same method as in Example 22, by a similar method thereto or by a combination of such a method with a conventional method using 2-hydroxy-N-methyl-acetamide, thiazolo[5,4-b]pyridin-2-yl-amine and 4-chloro-6-hydroxy-quinazoline.

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

Procedure: 5.93 g (29.4 mmol) of 4-nitrophenyl chloroformate are added portionwise and at room temperature to a suspension of 2.62 g (29.4 mmol) of 2-hydroxy-N-methylacetamide and 16.5 g (58.7 mmol) of supported diisopropylethylamine (Ps-DIEA from Argonaut, charge=3.56 mmol/g) in 250 ml of dichloromethane. Orbital stirring is continued at room temperature for 16 hours. The resin is filtered off and rinsed with 150 ml of dichloromethane, and the filtrate is concentrated under reduced pressure. 6 g of product are obtained in the form of a pale yellow solid (purity estimated at 70%), and are used without further purification in the following step. The resin is filtered off rinsed with 150 ml of dichloromethane the filtrate is concentrated under reduced pressure

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

Procedure: 5.93 g (29.4 mmol) of 4-nitrophenyl chloroformate are added portionwise and at room temperature to a suspension of 2.62 g (29.4 mmol) of 2-hydroxy-N-methylacetamide and 16.5 g (58.7 mmol) of supported diisopropylethylamine (Ps-DIEA from Argonaut, charge=3.56 mmol/g) in 250 ml of dichloromethane. Orbital stirring is continued at room temperature for 16 hours. The resin is filtered off and rinsed with 150 ml of dichloromethane, and the filtrate is concentrated under reduced pressure. 6 g of product are obtained in the form of a pale yellow solid (purity estimated at 70%), and are used without further purification in the following step. The resin is filtered off rinsed with 150 ml of dichloromethane the filtrate is concentrated under reduced pressure