Ethylenediamine → 2-Hydroxy-1,1-dimethyl-ethyl-amide

HRID 246561

反応式

HRID 246561 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]([NH:23][C:24]([CH3:28])([CH3:27])[CH2:25][OH:26])=[O:22])=[CH:19][N:18](COCC[Si](C)(C)C)[C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.FC(F)(F)C(O)=[O:40].C(N)CN>ClCCl>[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]([OH:40])=[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.[OH:26][CH2:25][C:24]([NH-:23])([CH3:28])[CH3:27]

参加物

6

反応物 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 712804242-(6-Fluoro-1-methyl-1H-indazol-3-yl)-N-(1-hydroxy-2-methylpropan-2-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

生成物 2

HCID 712796392-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acidHCID 866779892-Hydroxy-1,1-dimethyl-ethyl-amide収率 174.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

2-(6-Fluoro-1-methyl-1H-indazol-3-yl)-N-(1-hydroxy-2-methylpropan-2-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (0.08 g, 0.156 mmol), and trifluoroacetic acid (1 mL, 13.0 mmol) were stirred in dichloromethane for 15 h. The reaction mixture was concentrated in vacuo then ethylenediamine (1 mL, 14.8 mmol) in dichloromethane (5 mL) was added. After 1 h, the mixture was concentrated to dryness and water (1 mL) added. The solid precipitate was collected by filtration and dried to give 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl-amide (24 mg, 36%). MS (M+H)+=383; 1H NMR (DMSO-d6) δ: 9.07 (s, 1H), 8.60 (dd, J=8.7, 5.5 Hz, 1H), 8.37 (s, 1H), 7.91 (s, 1H), 7.66 (d, J=9.8 Hz, 1H), 7.15 (t, J=8.3 Hz, 1H), 4.14 (s, 3H), 3.62 (s, 2H), 1.45 (s, 6H).

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. concentrationthe mixture was concentrated to dryness and water (1 mL)
  3. additionadded
  4. filtrationThe solid precipitate was collected by filtration
  5. customdried

出典と根拠

ORDレコード
ord-7cd1dc268fce4e0eb78b95b2101fbd68
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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