Dimethylformamide → HCID 67366408, compound

HRID 410022Notes

Reaction equation

HRID 410022 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:25])[C:7]([C:16]3[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=3)=[C:8]([C:12]([F:15])([F:14])[F:13])[O:9]2)=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.[C:37]([NH:44][NH2:45])([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38].CN(C=O)C>C(Cl)Cl.CCOC(C)=O>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:25])[C:7]([C:16]3[CH:17]=[CH:18][C:19]([C:20]([NH:45][NH:44][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:22])=[CH:23][CH:24]=3)=[C:8]([C:12]([F:13])([F:14])[F:15])[O:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 70091tert-Butyl carbazateHCID 5426788HCID 5426788, compound

Product 1

HCID 67366408HCID 67366408, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(7-hydroxy-4-oxo-2-(trifluoromethyl)-4H-chromen-3-yl)benzoic acid (synthesis is described in PCT/US2010/024035) (1 equiv.), EDCI (1 equiv.), and BocNHNH2 (1 equiv.), in DCM and DMF (1:1) is stirred at 25° C. overnight, followed by an aqueous/EtOAc workup. Purification if necessary by column chromatography on silica gel to give the product.

Workup

  1. customPurification if necessary by column chromatography on silica gel
  2. customto give the product

Sources & evidence

ORD record
ord-87dde7bce5db42a1acdcf993178b9df2
Source dataset
uspto-grants-2014_06
Patent number
US08759548B2

Reaction notes

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