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

HRID 246591
ノート
印刷プレビュー

反応式

HRID 246591 の反応式
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:13]=[C:14]4[C:20]([C:21](O)=[O:22])=[CH:19][NH:18][C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.Cl.[CH3:36][C:37]1([NH2:43])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.O>CN(C=O)C.CN(C1C=CN=CC=1)C>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:13]=[C:14]4[C:20]([C:21]([NH:43][C:37]5([CH3:36])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]5)=[O:22])=[CH:19][NH:18][C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 3021577(1-Methylcyclohexyl)amine hydrochlorideHCID 712796392-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

生成物 1

HCID 712799592-(6-fluoro-1-methyl-1H-indazol-3-yl)-N-(1-methylcyclohexyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide収率 29.1%

試薬・触媒・溶媒 2

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

実験手順

To a stirred solution of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (70 mg, 0.22 mmol) in 6 mL of DMF were added EDCI (64 mg, 0.33 mmol) and DMAP (42 mg, 0.34 mmol), followed by the addition of 1-methylcyclohexanamine hydrochloride (50 mg, 0.33 mmol) in one portion at room temperature and stirred for 16 hours. The reaction mixture was poured into 35 mL of water, and filtered to give a crude product, which was purified by preparative-HPLC (Gemini 5u C18 150×21.2 mm; inject volume: 3 mL/inj, flow rate: 20 mL/min; wavelength: 214 nm and 254 nm; the gradient conditions were: 55% acetonitrile/45% water (0.1% trifluoroacetic acid, v/v) initially, proceeding to 88% acetonitrile/12% water (0.1% trifluoroacetic acid, v/v) in a linear fashion over 9 min.) to give 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-N-(1-methylcyclohexyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (26 mg, 28.4%) as a pale yellow solid. MS: (M+H)+=407; 1H NMR (300 MHz, DMSO): δ 12.68 (s, 1H), 9.10 (s, 1H), 8.45-8.40 (m, 2H), 7.85 (s, 1H), 7.71 (d, 1H, J=9.9 Hz), 7.20-7.14 (m, 1H), 4.17 (s, 3H), 2.33-2.29 (m, 2H), 2.03-2.00 (m, 1H), 1.53-1.46 (m, 10H).

後処理

  1. filtrationfiltered
  2. customto give a crude product, which
  3. customwas purified by preparative-HPLC (Gemini 5u C18 150×21.2 mm
  4. wait55% acetonitrile/45% water (0.1% trifluoroacetic acid, v/v) initially, proceeding to 88% acetonitrile/12% water (0.1% trifluoroacetic acid, v/v) in a linear fashion over 9 min.

出典と根拠

ORDレコード
ord-15be93852a9a414ab0ab803d872bed40
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08658646B2

反応ノート

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