Potassium Carbonate → 7-amino-2-cyano-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide

HRID 1184864Notes

Reaction equation

HRID 1184864 reaction equation
Br[C:2]1[C:3]([C:10]#[N:11])=[N:4][C:5]([C:8]#[N:9])=[CH:6][N:7]=1.[C:12]([C:14]([C:17]1[CH:18]=[C:19]([CH:35]=[CH:36][CH:37]=1)[C:20]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[C:25]([NH:30][C:31](=[O:34])[CH2:32][SH:33])[CH:24]=1)=[O:21])([CH3:16])[CH3:15])#[N:13].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[NH2:11][C:10]1[C:3]2[C:2](=[N:7][CH:6]=[C:5]([C:8]#[N:9])[N:4]=2)[S:33][C:32]=1[C:31]([NH:30][C:25]1[CH:24]=[C:23]([NH:22][C:20](=[O:21])[C:19]2[CH:35]=[CH:36][CH:37]=[C:17]([C:14]([C:12]#[N:13])([CH3:15])[CH3:16])[CH:18]=2)[CH:28]=[CH:27][C:26]=1[CH3:29])=[O:34]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 866801643-(2-cyanopropan-2-yl)-N-(3-(2-mercaptoacetamido)-4-methylphenyl)benzamideHCID 866801733-Bromopyrazine-2,6-dicarbonitrile

Product 1

HCID 547547657-amino-2-cyano-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamideYield 14.83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-bromopyrazine-2,6-dicarbonitrile 52 (17.06 mg, 0.082 mmol), 3-(2-cyanopropan-2-yl)-N-(3-(2-mercaptoacetamido)-4-methylphenyl)benzamide 16 (0.082 mmol, 30 mg) and potassium carbonate (13.54 mg, 0.098 mmol) in ethanol (1 mL) was stirred at 40° C. for 1 h. Quenched in 2N HCl solution and extracted with CH2Cl2. Organic layer was washed with brine, dried and evaporated. Purification by chromatography (5-10% EtOAc in CH2Cl2) gave the title compound 7-amino-2-cyano-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide 53 (6 mg, 14.83%). NMR (400 MHz, DMSO-d6) 1.75 (s, 6H), 2.22 (s, 3H), 7.29 (m, 2H), 7.60 (t, J=7.8 Hz, 2H), 7.75 (m, 1H), 7.81 (d, 2.0 Hz, 1H), 7.94 (d, J=Hz, J=7.8 Hz, 1H), 8.05 (t, J=2.0 Hz, 1H), 9.65 (s, 1H), 10.34 (s, 1H). (m/z)=496 (M+H)+.

Workup

  1. customQuenched in 2N HCl solution
  2. extractionextracted with CH2Cl2
  3. washOrganic layer was washed with brine
  4. customdried
  5. customevaporated
  6. customPurification by chromatography (5-10% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-853c20bd08104a36a523f9e069a51515
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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