Ethyl orthoformate → HCID 67055373, compound

HRID 603000Notes

Reaction equation

HRID 603000 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH:14]2[CH2:17][N:16]([C@@H:18]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[C:19]3[CH:20]=[C:21]([C:25](=[NH:28])[NH:26][OH:27])[CH:22]=[CH:23][CH:24]=3)[CH2:15]2)[C:10]([F:13])([CH3:12])[CH3:11])[CH:5]=[C:6]([F:8])[CH:7]=1.[CH:36](OCC)(OCC)OCC>C1(C)C(C)=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH:14]2[CH2:15][N:16]([C@@H:18]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[C:19]3[CH:20]=[C:21]([C:25]4[N:28]=[CH:36][O:27][N:26]=4)[CH:22]=[CH:23][CH:24]=3)[CH2:17]2)[C:10]([F:13])([CH3:12])[CH3:11])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 178455686HCID 178455686, compound

Product 1

HCID 67055373HCID 67055373, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
127.5 °C

Procedure

A mixture of 70 mg (0.125 mmol) of 3-[(S)-{3-[(1S)-1-(3-bromo-5-fluoro phenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl}(4-chlorophenyl)methyl]-N-hydroxybenzenecarboximidamide, 1.5 mL of triethyl orthoformate, and 2 mL of xylene was stirred for 4 h at 125-130° C. Then it was concentrated, and the residue was purified by silica gel chromatography with hexanes/acetone to afford the title compound as a white solid; Mass Spectrum: m/e=572 (M+1, 35Cl), 574 (M+1, 37Cl).

Workup

  1. concentrationThen it was concentrated
  2. customthe residue was purified by silica gel chromatography with hexanes/acetone

Sources & evidence

ORD record
ord-a1cced2b63ed47b39560c44fb06fc475
Source dataset
uspto-grants-2011_03
Patent number
US07906652B2

Reaction notes

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