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

HRID 1184933Notes

Reaction equation

HRID 1184933 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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)+.

Workup

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

Sources & evidence

ORD record
ord-4c9afb1243fa4a63b008e082fac30634
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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