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

HRID 246620

反応式

HRID 246620 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:17]=[C:16]4[C:18]([C:21](O)=[O:22])=[CH:19][NH:20][C:15]4=[N:14][CH:13]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.[NH2:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[C:28]#[N:29].CCN=C=NCCCN(C)C.O>CN(C1C=CN=CC=1)C.CN(C=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:17]=[C:16]4[C:18]([C:21]([NH:24][C:25]5[CH:32]=[CH:31][CH:30]=[C:27]([C:28]#[N:29])[CH:26]=5)=[O:22])=[CH:19][NH:20][C:15]4=[N:14][CH:13]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 167023-AminobenzonitrileHCID 712800962-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

生成物 1

HCID 712801652-(6-chloro-1-methyl-1H-indazol-3-yl)-N-(3-cyanophenyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide収率 20.3%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid (70 mg, 0.23 mmol), 3-aminobenzonitrile (41 mg, 0.344 mmol), EDCI (88 mg, 0.46 mmol) and DMAP (56 mg, 0.46 mmol) in DMF (5 mL) was stirred at room temperature for 16 hours. Then the mixture was poured into water (5 mL) and filtered to give a crude product. The crude product was triturated with DMSO and MeOH, then decanted and dried to give 2-(6-chloro-1-methyl-1H-indazol-3-yl)-N-(3-cyanophenyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (20 mg, 20%) as a white solid. MS: (M+H)+=428; 1H NMR (300 MHz, DMSO): δ 10.55 (s, 1H), 8.81 (s, 1H), 8.55-8.50 (m, 2H), 8.15 (brs, 1H), 8.03-8.00 (m, 1H), 7.92 (s, 1H), 7.59 (d, 1H, J=8.1 Hz), 7.48 (d, 1H, J=7.8 Hz), 7.26 (d, 1H, J=7.5 Hz), 4.14 (s, 3H).

後処理

  1. filtrationfiltered
  2. customto give a crude product
  3. customThe crude product was triturated with DMSO and MeOH
  4. customdecanted
  5. customdried

出典と根拠

ORDレコード
ord-f79bd9aebb64478db44d6052fdbcd3f5
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

関連ノート

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