Dimethylacetamide → HCID 68428624, compound

HRID 642515Notes

Reaction equation

HRID 642515 reaction equation
Cl[C:2]1[N:3]=[C:4]([C:25]([NH:27][CH2:28][C:29]([OH:31])=[O:30])=[O:26])[C:5]([OH:24])=[C:6]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][N:8]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[C:7]=12.C[C:33]([N:35](C)C)=O>CS(C)=O.[C-]#N.[C-]#N.[Zn+2].[Zn].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].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.[Fe+2]>[C:33]([C:2]1[N:3]=[C:4]([C:25]([NH:27][CH2:28][C:29]([OH:31])=[O:30])=[O:26])[C:5]([OH:24])=[C:6]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][N:8]([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[C:7]=12)#[N:35]

Participants

8

Reactant 2

HCID 31374DimethylacetamideHCID 24756645HCID 24756645, compound

Product 1

HCID 68428624HCID 68428624, compound

Reagents, catalysts & solvents 5

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of {[7-chloro-1-(4-fluoro-phenyl)-4-hydroxy-3-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carbonyl]-amino}-acetic acid (30 mg), Zn(CN)2 (4.0 mg), Zn dust (0.5 mg), Pd2(dba)3 (3.2 mg), dppf (3.8 mg) in DMA (1 mL) was heated to 120° C. for 90 min; then the mixture was cooled, diluted with DMSO and purified by C18 reverse phase chromatography to give the desired title compound (11 mg). The title compound, ESI MS (m/z): 431 (M+H)+.

Workup

  1. temperaturethen the mixture was cooled
  2. custompurified by C18 reverse phase chromatography

Sources & evidence

ORD record
ord-d8440eb5e9f341ebb472a0c031c9e38a
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

Loading…