Dimethylacetamide → HCID 24780985, compound

HRID 706253Notes

Reaction equation

HRID 706253 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:9]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]=2)[C:5]([OH:26])=[C:4]([C:27]([NH:29][CH2:30][C:31]([OH:33])=[O:32])=[O:28])[N:3]=1.[CH3:34][N:35](C)C(=O)C>C(OCC)(=O)C.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].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Zn].[C-]#N.[Zn+2].[C-]#N>[C:34]([C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:9]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]=2)[C:5]([OH:26])=[C:4]([C:27]([NH:29][CH2:30][C:31]([OH:33])=[O:32])=[O:28])[N:3]=1)#[N:35]

Participants

8

Reactant 2

HCID 31374DimethylacetamideHCID 11419901HCID 11419901, compound

Product 1

HCID 24780985HCID 24780985, compound

Reagents, catalysts & solvents 5

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

[(1-Cyano-4-hydroxy-6,7-diphenoxy-isoquinoline-3-carbonyl)-amino]-acetic acid was prepared by adding 76 mg (0.164 mmol) of [(1-chloro-4-hydroxy-6,7-diphenoxy-isoquinoline-3-carbonyl)-amino]-acetic acid (prepared according to US 2006/0217416), 7.3 mg (0.008 mmol) tris(dibenzylideneacetone)dipalladium(0), 9.0 mg (0.016 mmol) 1,1′-bis(diphenylphosphino) ferrocene, 1.3 mg (0.020 mmol) zinc dust, and 12 mg (0.10 mmol) zinc cyanide to 0.35 mL of N,N-dimethylacetamide. The resultant mixture was heated at 115° C. for 3 hours under a nitrogen atmosphere, and then cooled to room temperature. The mixture was diluted with ethyl acetate and extracted three times with aqueous sodium bicarbonate and twice with 1 N NaOH solutions. The basic aqueous extracts were acidified with concentrated HCl, and extracted three times with ethyl acetate. The organic extracts were dried over sodium sulfate and concentrated to give 29 mg of the title compound as a white solid; MS (ESI−): m/z 454.0 (M−1)

Workup

  1. custom[(1-Cyano-4-hydroxy-6,7-diphenoxy-isoquinoline-3-carbonyl)-amino]-acetic acid was prepared
  2. extractionextracted three times with aqueous sodium bicarbonate
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe organic extracts were dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7a21e750b1c84638907fdf41d74dc2f3
Source dataset
uspto-grants-2015_11
Patent number
US09174976B2

Reaction notes

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