Potassium Carbonate → HCID 67125601, compound

HRID 1184913Notes

Reaction equation

HRID 1184913 reaction equation
Cl[C:2]1[N:7]=[C:6]2[S:8][C:9]([C:11]([NH:13][C:14]3[CH:19]=[C:18]([NH:20][C:21](=[O:33])[C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([C:31]#[N:32])([CH3:30])[CH3:29])[CH:23]=4)[CH:17]=[CH:16][C:15]=3[CH3:34])=[O:12])=[CH:10][C:5]2=[N:4][CH:3]=1.[C:35](=O)([O-])[O-].[K+].[K+].[Cl-].C[Zn+]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:31]([C:28]([C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[C:21]([NH:20][C:18]1[CH:17]=[CH:16][C:15]([CH3:34])=[C:14]([NH:13][C:11]([C:9]2[S:8][C:6]3=[N:7][C:2]([CH3:35])=[CH:3][N:4]=[C:5]3[CH:10]=2)=[O:12])[CH:19]=1)=[O:33])([CH3:30])[CH3:29])#[N:32]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 866801803-chloro-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamideHCID 178477797HCID 178477797, compound

Product 1

HCID 67125601HCID 67125601, compoundYield 31.3%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 3-chloro-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide (0.204 mmol, 100 mg), potassium carbonate (0.408 mmol, 56.4 mg), 1,1′-bis(diphenylphosphino)ferrocenedichloro palladium(II) (0.020 mmol, 14.77 mg) in THF, was added methylzinc chloride (2.041 mmol, 1020 μl) and stirred overnight at 60° C. The reaction was quenched in water, extracted with ethyl acetate. Organic layer was dried and concentrated under reduced pressure. Crude product was purified with HPLC to give N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-3-methylthieno[2,3-b]pyrazine-6-carboxamide 96l (30 mg, 31%). NMR (400 MHz, DMSO-d6) 1.76 (s, 6H), 2.26 (s, 3H), 2.68 (s, 3H), 7.31 (d, J=8.6 Hz, 1H), 7.62 (m, 2H), 7.76 (d, J=8.6 Hz, 1H), 7.86 (d, J=2.0 Hz, 1H), 7.95 (d, J=7.8 Hz, 1H), 8.06 (s, 1H), 8.50 (s, 1H), 8.78 (s, 1H), 10.36 (s, 1H), 10.45 (s, 1H). (m/z)=471 (M+H)+.

Workup

  1. customThe reaction was quenched in water
  2. extractionextracted with ethyl acetate
  3. customOrganic layer was dried
  4. concentrationconcentrated under reduced pressure
  5. customCrude product was purified with HPLC

Sources & evidence

ORD record
ord-84f809fcfb1742139567342d2193b405
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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