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

반응식

HRID 17102 반응식
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

참가 물질

9

반응물 6

HCID 6228DimethylformamideHCID 6422Trifluoroacetic acid2회HCID 15655Cyclopropanecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 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

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 962Water용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-eab24ac768e847f2b55ea80beb8050ec
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737279B2

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