Dimethylformamide → HCID 69042852, compound

HRID 1259281Notes

Reaction equation

HRID 1259281 reaction equation
BrC1C=[C:6]([CH2:8][C:9]2[C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[C:12](=[O:19])[NH:11][N:10]=2)[CH:5]=CN=1.C([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])C.[C]=[O:28].CN(C)[CH:31]=[O:32]>CO>[O:19]=[C:12]1[C:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:18]=2[C:9]([CH2:8][C:6]2[CH:24]=[CH:23][N:22]=[C:25]([C:26]([O:32][CH3:31])=[O:28])[CH:5]=2)=[N:10][NH:11]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 87671472HCID 87671472, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 69042852HCID 69042852, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of EXAMPLE 66B (800 mg, 2.5 mmol), dichloro(1,1′-ferrocenylbis(diphenyl-phosphine))palladium(II)dichloromethane (125 mg, 0.15 mmol) and triethylamine (1 ml) in a mixture of methanol (40 ml) and N,N-dimethylformamide (16 ml) was heated at 110° C. in a pressure vessel under 30 psi of carbon monoxide for 16 hours. After cooling, the solid material was filtered off, and the filtrate was concentrated. The residual solid was washed with methanol, and dried to provide the title compound. MS (DCI/NH3) m/z 300 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid material was filtered off
  3. concentrationthe filtrate was concentrated
  4. washThe residual solid was washed with methanol
  5. customdried

Sources & evidence

ORD record
ord-b50e080a7bdc42a48356281e51d1c877
Source dataset
uspto-grants-2013_06
Patent number
US08466150B2

Reaction notes

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