Water → N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-2-ethoxythieno[2,3-b]pyrazine-6-carboxamide

HRID 1184933ノート

反応式

HRID 1184933 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:22])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([C:20]#[N:21])([CH3:19])[CH3:18])[CH:12]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].C(N(CC)CC)C.[CH2:30]([O:32][C:33]1[N:34]=[C:35]2[CH:41]=[C:40]([C:42](Cl)=[O:43])[S:39][C:36]2=[N:37][CH:38]=1)[CH3:31].O>C(Cl)Cl>[C:20]([C:17]([C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[C:10]([NH:9][C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([NH:1][C:42]([C:40]2[S:39][C:36]3=[N:37][CH:38]=[C:33]([O:32][CH2:30][CH3:31])[N:34]=[C:35]3[CH:41]=2)=[O:43])[CH:3]=1)=[O:22])([CH3:19])[CH3:18])#[N:21]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 67125542N-(3-amino-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamideHCID 866801842-Ethoxythieno[2,3-b]pyrazine-6-carbonyl chloride

生成物 1

HCID 67125646N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-2-ethoxythieno[2,3-b]pyrazine-6-carboxamide収率 7.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of N-(3-amino-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide 5 (38 mg, 0.132 mmol) and triethylamine (0.092 mL, 0.66 mmol) in CH2Cl2 (1 mL) was added 2-ethoxythieno[2,3-b]pyrazine-6-carbonyl chloride (32 mg, 0.132 mmol) in CH2Cl2 (1 mL) and stirred overnight at rt. Water was added and extracted with CH2Cl2. Organic layer was washed with water, dried and evaporated. Purification by HPLC gave N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-2-ethoxythieno[2,3-b]pyrazine-6-carboxamide (5 mg, 7%). 1H-NMR (400 MHz, DMSO-d6). 1.42 (t, J=7.0 Hz, 3H), 1.76 (s, 6H), 2.26 (s, 3H), 4.46 (q, J=7.0 Hz and 14.0 Hz, 2H), 7.31 (d, 8.2 Hz, 1H), 7.58-7.66 (m, 2H), 7.76 (d, J=7.8 Hz, 1H), 7.87 (d, J=1.9 Hz, 1H), 7.95 (d, J=7.8 Hz, 1H), 8.05 (s, 1H), 8.35 (s, 1H), 8.41 (s, 1H), 10.35 (s, 1H), 10.37 (s, 1H). (m/z)=500 (M+H)+.

後処理

  1. extractionextracted with CH2Cl2
  2. washOrganic layer was washed with water
  3. customdried
  4. customevaporated
  5. customPurification by HPLC

出典と根拠

ORDレコード
ord-4c9afb1243fa4a63b008e082fac30634
出典データセット
uspto-grants-2014_03
特許番号
US08669256B2

反応ノート

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