Dimethylformamide → N-[[6-[1,6-dihydro-1-methyl-4-(methylamino)imidazo[4,5-d]pyrrolo[2,3-b]pyridin-7-yl]-2-pyridinyl]methyl]-cyclopropanecarboxamide

HRID 17102

Reaction equation

HRID 17102 reaction equation
Cl.[CH3:2][N:3]([CH3:12])[CH2:4][CH2:5][CH2:6][N:7]=[C:8]=[N:9][CH2:10]C.O[N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=N1.C([N:26]([CH:29](C)C)CC)(C)C.[CH:32]1([C:35]([OH:37])=O)[CH2:34][CH2:33]1.[C:38](O)([C:40](F)(F)F)=O.C[N:46](C)C=O>O.CO>[CH3:2][N:3]1[C:4]2=[C:38]3[CH:40]=[C:10]([C:18]4[N:14]=[C:22]([CH2:17][NH:16][C:35]([CH:32]5[CH2:34][CH2:33]5)=[O:37])[CH:21]=[CH:20][CH:19]=4)[NH:9][C:8]3=[N:7][C:6]([NH:26][CH3:29])=[C:5]2[N:46]=[CH:12]1

Participants

9

Reactant 6

HCID 6228DimethylformamideHCID 6422Trifluoroacetic acid2×HCID 15655Cyclopropanecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 57393213N-[[6-[1,6-dihydro-1-methyl-4-(methylamino)imidazo[4,5-d]pyrrolo[2,3-b]pyridin-7-yl]-2-pyridinyl]methyl]-cyclopropanecarboxamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

To a mixture of A215 (0.020 g, 0.065 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.019 g, 0.098 mmol), 1-hydroxybenzotriazole (0.013 g, 0.098 mmol), and diisopropylethylamine (0.034 mL, 0.195 mmol) in anhydrous dimethylformamide (2 mL) was added cyclopropylcarboxylic acid (8.00 μL, 0.098 mmol). The reaction mixture was stirred at room temperature overnight. Concentration under pressure followed by purification by flash silica gel chromatography using a 5% mixture of methanol in dichloromethane afforded 0.012 g (50%) of A218 as a yellow solid. The compound had an HPLC retention time=1.99 min. (Column: Chromolith SpeedROD 4.6×50 mm—4 min.; Solvent A=10% MeOH, 90% H2O, and 0.1% TFA; Solvent B=90% MeOH, 10% H2O, and 0.1% TFA) and a LC/MS M+1=376.40.

Workup

  1. concentrationConcentration under pressure
  2. customfollowed by purification by flash silica gel chromatography
  3. customafforded 0.012 g (50%) of A218 as a yellow solid

Sources & evidence

ORD record
ord-eab24ac768e847f2b55ea80beb8050ec
Source dataset
uspto-grants-2010_06
Patent number
US07737279B2

Linked notes

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