Sodium Carbonate → N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-7-oxo-6,7-dihydrothieno[2,3-b]pyrazine-6-carboxamide

HRID 1184917Notes

Reaction equation

HRID 1184917 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:24]=[CH:25][CH:26]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([NH:19][C:20](=[O:23])[CH2:21][SH:22])[CH:13]=1)=[O:10])([CH3:5])[CH3:4])#[N:2].Br[C:28]1[C:29]([C:34](OC)=[O:35])=[N:30][CH:31]=[CH:32][N:33]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)C>[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:24]=[CH:25][CH:26]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([NH:19][C:20]([CH:21]2[S:22][C:28]3=[N:33][CH:32]=[CH:31][N:30]=[C:29]3[C:34]2=[O:35])=[O:23])[CH:13]=1)=[O:10])([CH3:4])[CH3:5])#[N:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 13318551Methyl 3-bromopyrazine-2-carboxylateHCID 866801643-(2-cyanopropan-2-yl)-N-(3-(2-mercaptoacetamido)-4-methylphenyl)benzamide

Product 1

HCID 67125612N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-7-oxo-6,7-dihydrothieno[2,3-b]pyrazine-6-carboxamideYield 43.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(2-cyanopropan-2-yl)-N-(3-(2-mercaptoacetamido)-4-methylphenyl)benzamide 16 (0.054 mmol, 20 mg), methyl 3-bromopyrazine-2-carboxylate 101 (0.054 mmol, 11.8 mg) and Na2CO3 (1.2 eq, 7 mg) in ethanol (1 mL) was stirred overnight at 70° C. The reaction mixture was quenched in cold 1N HCl solution and extracted with CH2Cl2. Organic layer was dried and evaporated. Purification by chromatography (0-10% methanol in CH2Cl2) gave N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-7-oxo-6,7-dihydrothieno[2,3-b]pyrazine-6-carboxamide 102 (11 mg, 42.9%). NMR (400 MHz, DMSO-d6) 1.77 (s, 6H), 2.35 (s, 3H), 7.15 (d, J=8.6 Hz, 1H), 7.48 (dd, J=8.2 Hz and 2.3 Hz, 1H), 7.59 (t, J=7.8 Hz, 1H), 7.74 (d, J=7.8 Hz, 1H), 7.97 (d, J=7.8 Hz, 1H), 8.07 (t, J=2.0 Hz, 1H), 8.54 (br s, 1H), 8.62 (br s, 1H), 8.66 (d, J=1.6 Hz, 1H), 10.29 (s, 1H). (m/z)=473 (M+H)+.

Workup

  1. customThe reaction mixture was quenched in cold 1N HCl solution
  2. extractionextracted with CH2Cl2
  3. customOrganic layer was dried
  4. customevaporated
  5. customPurification by chromatography (0-10% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-c2a0fbe1b05a4717bc7acf0d53921887
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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