Water → N-(1-(dimethylamino)-2-methylpropan-2-yl)-2-(6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 246689노트

반응식

HRID 246689 반응식
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[N:12]=[C:13]4[C:19]([C:20]([OH:22])=O)=[CH:18][NH:17][C:14]4=[N:15][CH:16]=3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.[CH3:23][N:24]([CH3:30])[CH2:25][C:26]([CH3:29])([NH2:28])[CH3:27].O>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:23][N:24]([CH3:30])[CH2:25][C:26]([NH:28][C:20]([C:19]1[C:13]2[C:14](=[N:15][CH:16]=[C:11]([C:6]3[C:5]4[C:9](=[CH:10][C:2]([CH3:1])=[CH:3][CH:4]=4)[NH:8][N:7]=3)[N:12]=2)[NH:17][CH:18]=1)=[O:22])([CH3:29])[CH3:27]

참가 물질

6

반응물 3

HCID 962WaterHCID 226843(2-Amino-2-methylpropyl)dimethylamineHCID 712798942-(6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

생성물 1

HCID 71280149N-(1-(dimethylamino)-2-methylpropan-2-yl)-2-(6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide수율 16.5%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 2-(6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (100 mg, 0.34 mmol), DCI (123 mg, 0.64 mmol) and DMAP (110 mg, 0.90 mmol) in 6 mL of DMF was added N1,N1,2-trimethylpropane-1,2-diamine (100 mg, 0.86 mmol) in one portion at room temperature, then the mixture was stirred for 16 hours. The reaction mixture was poured into 40 mL of water, filtered and the filter cake was purified by column chromatography (silica gel, 200-300 mesh, eluting with a mixture of methanol and THF (1:3, v/v) to give N-(1-(dimethylamino)-2-methylpropan-2-yl)-2-(6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (22 mg, 16.5%) as a yellow solid. MS: (M+H)+=392; 1H NMR (300 MHz, DMSO): δ 13.38 (s, 1H), 12.90 (brs, 1H), 9.15 (s, 1H), 8.47 (d, 1H, J=8.4 Hz), 8.37 (s, 1H), 7.97 (s, 1 h), 7.45 (s, 1H), 7.10 (d, 1H, J=8.4 Hz), 2.74 (s, 2H), 2.52 (s, 3H), 2.29 (s, 3H), 2.26 (s, 3H), 2.01 (s, 6H).

후처리

  1. filtrationfiltered
  2. customthe filter cake was purified by column chromatography (silica gel, 200-300 mesh
  3. washeluting with a mixture of methanol and THF (1:3

출처 및 근거

ORD 기록
ord-fae14794ccee4d9880c36e3407e93020
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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