Sodium Carbonate → HCID 67125573, compound

HRID 1184930Notes

Reaction equation

HRID 1184930 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:23]=[CH:24][CH:25]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([C:19](=[O:22])[CH2:20][SH:21])[CH:13]=1)=[O:10])([CH3:5])[CH3:4])#[N:2].Cl[C:27]1[C:28]([C:33]#[N:34])=[N:29][CH:30]=[CH:31][N:32]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[NH2:34][C:33]1[C:28]2[C:27](=[N:32][CH:31]=[CH:30][N:29]=2)[S:21][C:20]=1[C:19]([C:14]1[CH:13]=[C:12]([NH:11][C:9](=[O:10])[C:8]2[CH:23]=[CH:24][CH:25]=[C:6]([C:3]([C:1]#[N:2])([CH3:4])[CH3:5])[CH:7]=2)[CH:17]=[CH:16][C:15]=1[CH3:18])=[O:22]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2924653-Chloropyrazine-2-carbonitrileHCID 86680183HCID 86680183, compound

Product 1

HCID 67125573HCID 67125573, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(2-cyanopropan-2-yl)-N-(3-(2-mercaptoacetyl)-4-methylphenyl)benzamide 115 (0.094 mmol, 33 mg), 3-chloropyrazine-2-carbonitrile (0.094 mmol, 13 mg) and sodium carbonate (0.112 mmol, 12 mg) in ethanol (1 mL) was stirred 2 h at 50° C. Quenched in 1N HCl solution and extracted with CH2Cl2. Organic layer was dried and evaporated. Purification by HPLC gave N-(3-(7-aminothieno[2,3-b]pyrazine-6-carbonyl)-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide 116 (9 mg, 21%). NMR (400 MHz, DMSO-d6) 1.74 (s, 6H), 2.27 (s, 3H), 7.37 (d, J=8.6 Hz, 1H), 7.60 (t, J=7.8 Hz, 1H), 7.76 (d, J=7.8 Hz, 1H), 7.81 (dd, J=8.2 Hz and 2.3 Hz), 7.95 (m, 2H), 8.04 (m, 3H), 8.82 (s, 2H), 10.44 (s, 1H). (m/z)=457 (M+H)+.

Workup

  1. customQuenched in 1N HCl solution
  2. extractionextracted with CH2Cl2
  3. customOrganic layer was dried
  4. customevaporated
  5. customPurification by HPLC

Sources & evidence

ORD record
ord-229351b8fad345c48bbb2c5228b48e3e
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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