HCID 68182666, compound → HCID 86669676, compound

HRID 1623933Notes

Reaction equation

HRID 1623933 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([NH:12][C:13]([C:15]2[C:16]3[CH2:17][C@H:18]4[CH2:31][C@H:19]4[C:20]=3[N:21]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=3[F:30])[N:22]=2)=[O:14])[CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH:8]1[CH2:11][CH:10]([NH:12][C:13]([C:15]2[C:16]3[CH2:17][C@H:18]4[CH2:31][C@H:19]4[C:20]=3[N:21]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=3[F:30])[N:22]=2)=[O:14])[CH2:9]1

Participants

3

Reactant 1

HCID 68182666HCID 68182666, compound

Product 1

HCID 86669676HCID 86669676, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

3-{[(1aR,5aR)-2-(2,4-Difluoro-phenyl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carbonyl]-amino}-azetidine-1-carboxylic acid tert-butyl ester was dissolved in 20% TFA/DCM. The reaction mixture was stirred at room temperature for 1 h. The solvent was evaporated, and the residue was purified by cation exchange resin to give (1aR,5aR)-2-(2,4-difluoro-phenyl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid (azetidin-3-yl)-amide. This material was mixed with 3-bromo-1,1,1-trifluoropropane and Et3N in IPA. The reaction was heated under microwave irradiation for 1 h at 150° C. The mixture was purified by preparative HPLC to provide the title compound. LCMS m/z=427.3 [M+H]+.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by cation exchange resin

Sources & evidence

ORD record
ord-09209a38af5b42dcbc4a7c45a67aaa53
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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