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

HRID 1184933노트

반응식

HRID 1184933 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-4c9afb1243fa4a63b008e082fac30634
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08669256B2

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