Tert-Butylamine → N-tert-butyl-2-(1-methyl-5-(trifluoromethyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

HRID 246639ノート

反応式

HRID 246639 の反応式
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([F:14])([F:13])[F:12])=[CH:8][CH:9]=2)[C:4]([C:15]2[N:20]=[C:19]3[C:21]([C:24](O)=[O:25])=[CH:22][NH:23][C:18]3=[N:17][CH:16]=2)=[N:3]1.[CH3:27][C:28]([NH2:31])([CH3:30])[CH3:29].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(N(CC)CC)C>ClCCl.O>[C:28]([NH:31][C:24]([C:21]1[C:19]2=[N:20][C:15]([C:4]3[C:5]4[C:10](=[CH:9][CH:8]=[C:7]([C:11]([F:13])([F:12])[F:14])[CH:6]=4)[N:2]([CH3:1])[N:3]=3)=[CH:16][N:17]=[C:18]2[NH:23][CH:22]=1)=[O:25])([CH3:30])([CH3:29])[CH3:27]

参加物

8

反応物 5

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 712796662-(1-methyl-5-(trifluoromethyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid

生成物 1

HCID 71280444N-tert-butyl-2-(1-methyl-5-(trifluoromethyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide収率 15.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 2-(1-methyl-5-(trifluoromethyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid (100 mg, 0.28 mmol), 2-methylpropan-2-amine (20 mg, 0.28 mmol), HOBt (149 mg, 1.12 mmol), EDCI (211 mg, 1.12 mmol) and triethylamine (133 mg, 1.12 mmol) in dichloromethane (15 mL) was stirred at room temperature for 15 hours, then water (30 mL) was added, product extracted with dichloromethane (3×30 mL), the combined organic layers were concentrated and the residue was purified by column chromatography (silica gel, 200-300 mesh, eluting with petroleum ether/ethyl acetate=10:1) to give N-tert-butyl-2-(1-methyl-5-(trifluoromethyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (18 mg, 15.6%) as an orange solid. LCMS: (M+H)+=417; 1H NMR (300 MHz, DMSO): δ 12.89 (s, 1H), 9.06 (s, 1H), 8.71 (s, 1H), 8.44 (s, 1H), 8.05 (d, 1H, J=9.0 Hz), 7.93 (s, 1H), 7.84 (d, 1H, J=9.0 Hz), 4.28 (s, 3H), 1.47 (s, 9H).

後処理

  1. extractionproduct extracted with dichloromethane (3×30 mL)
  2. concentrationthe combined organic layers were concentrated
  3. customthe residue was purified by column chromatography (silica gel, 200-300 mesh, eluting with petroleum ether/ethyl acetate=10:1)

出典と根拠

ORDレコード
ord-1c0f9b7f1bf64b2995fa56d2402bfc56
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

反応ノート

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