Trimethylsilyldiazomethane → HCID 23582094, compound

HRID 238794Notes

Reaction equation

HRID 238794 reaction equation
[N:1]1[NH:2][N:3]=[N:4][C:5]=1[CH2:6][C:7]([NH:30][C:31](=[O:43])[C:32]1[CH:37]=[CH:36][C:35]([F:38])=[C:34]([C:39]([F:42])([F:41])[F:40])[CH:33]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]([F:29])([F:28])[F:27])[CH:20]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]([F:18])([F:17])[F:16])[CH:9]=1.[N+](=[CH:46][Si](C)(C)C)=[N-]>C1COCC1.CO>[F:38][C:35]1[CH:36]=[CH:37][C:32]([C:31]([NH:30][C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]([F:16])([F:17])[F:18])[CH:9]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]([F:27])([F:28])[F:29])[CH:20]=2)[CH2:6][C:5]2[N:4]=[N:3][N:2]([CH3:46])[N:1]=2)=[O:43])=[CH:33][C:34]=1[C:39]([F:40])([F:41])[F:42]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 23582027HCID 23582027, compound

Product 1

HCID 23582094HCID 23582094, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(2-(2H-tetrazol-5-yl)-1,1-bis(3-(trifluoromethoxy)phenyl)ethyl)-4-fluoro-3-(trifluoromethyl)benzamide (18 mg, 0.029 mmol) in THF (0.4 mL) and MeOH (0.1 mL) at rt was added (diazomethyl)trimethylsilane (0.02 mL, 2.0 M solution). The resulting solution was stirred at rt for 20 min. The solvents were evaporated and resulting residue was purified by ISCO flash chromatography (silica gel, hexane/EtOAc) to give 4-fluoro-N-(2-(2-methyl-2H-tetrazol-5-yl)-1,1-bis(3-(trifluoromethoxy)phenyl)ethyl)-3-(trifluoromethyl)benzamide (Example 281, 11 mg, yield: 60%). LCMS: RT=4.06 min [M+H] 638.23, [M+Na] 661.26 (Phenomenex Luna C18 column, 4.6×50 mm eluting with 10-90% MeOH/H2O over 4 minutes containing 0.1% TFA; 4 mL/min, monitoring at 220 nm).

Workup

  1. customThe solvents were evaporated
  2. customresulting residue
  3. customwas purified by ISCO flash chromatography (silica gel, hexane/EtOAc)

Sources & evidence

ORD record
ord-0e8ae317a90749c694557ad34700010c
Source dataset
uspto-grants-2014_02
Patent number
US08642576B2

Reaction notes

Loading…