N-methyl-N-[[(2S)-pyrrolidin-2-yl]methyl]cyclopropanamine

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

Procedure: A mixture of {5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-acetic acid (104 mg, 0.2 mmol), cyclopropyl-methyl-(S)-1-pyrrolidin-2-ylmethyl-amine (53 mg, 0.34 mmol), HOBt (43 mg, 0.32 mmol), EDAC (65 mg, 0.34 mmol) and TEA (0.06 mL) in DMF (3 mL) was stirred at rt for 48 hours. The reaction was concentrated, diluted with sodium bicarbonate and extracted with DCM. The combined DCM was dried, concentrated and purified on a silica gel column to give 89 mg (68%) of the titled compound. The reaction was concentrated diluted with sodium bicarbonate extracted with DCM The combined DCM was dried concentrated purified on a silica gel column

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

Procedure: A mixture of 5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (165 mg, 0.33 mmol), cyclopropyl-methyl-(S)-1-pyrrolidin-2-ylmethyl-amine (65 mg, 0.46 mmol), HOBt (687 mg, 0.5 mmol), EDAC (101 mg, 0.53 mmol) and TEA (0.1 mL) in DMF (4 mL) was stirred at rt for 48 hours. The reaction was concentrated, diluted with sodium bicarbonate, extracted with DCM. The combined DCM was dried, concentrated and purified on a silica gel column to give the titled compound. The reaction was concentrated diluted with sodium bicarbonate extracted with DCM The combined DCM was dried concentrated purified on a silica gel column

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

Procedure: To a solution of (S)-pyrrolidine-2-carboxylic acid cyclopropyl-methyl-amide in THF at 0° C. was added borane (2 eq., 1 M in THF) dropwise. The mixture was allowed to warm up to rt then heated to reflux for 24 hours. The cooled reaction was acidified with HCl and heated at 75° C. for 10 mins. The mixture was concentrated, basified with 2N NaOH and extracted with 10% methanol in DCM. The combined DCM was dried and concentrated to give cyclopropyl-methyl-(S)-1-pyrrolidin-2-ylmethyl-amine. then heated to reflux for 24 hours The cooled reaction heated at 75° C. for 10 mins The mixture was concentrated extracted with 10% methanol in DCM The combined DCM was dried concentrated