Methanesulfonyl chloride → HCID 71257545, compound

HRID 710151Notes

Reaction equation

HRID 710151 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:14]=[C:13]([N:15]2[CH:19]=[N:18][N:17]=[N:16]2)[CH:12]=[CH:11][C:10]=1[C:20]1[CH:21]=[CH:22][C:23]2[O:27][C:26]([CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[N:25][C:24]=2[CH:34]=1.[CH3:35][S:36](Cl)(=[O:38])=[O:37].C(Cl)Cl.O>C(Cl)Cl>[F:8][C:9]1[CH:14]=[C:13]([N:15]2[CH:19]=[N:18][N:17]=[N:16]2)[CH:12]=[CH:11][C:10]=1[C:20]1[CH:21]=[CH:22][C:23]2[O:27][C:26]([CH:28]3[CH2:29][CH2:30][N:31]([S:36]([CH3:35])(=[O:38])=[O:37])[CH2:32][CH2:33]3)=[N:25][C:24]=2[CH:34]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 21908982Water methylene chlorideHCID 710900805-(2-fluoro-4-(1H-tetrazol-1-yl)phenyl)-2-(piperidin-4-yl)benzo[d]oxazole 2,2,2-trifluoroacetate

Product 1

HCID 71257545HCID 71257545, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-[2-fluoro-4-(1H-tetrazol-1-yl)-phenyl]-2-(piperidin-4-yl)benzo[d]oxazole 2,2,2-trifluoroacetate (30 mg, 0.06 mmol) was dissolved in DCM (5 ml) and added TEA (60 mg, 0.6 mmol) and stirred the mixture at rt for 30 mins. To this mixture added methanesulphonyl chloride (14 mg, 0.12 mmol) and stirred at rt for 2 h. Work up (DCM/H2O) followed by purification on combiflash using a gradient mixture of EtOAc and Petether (7:3) as eluent afforded the titled compound (17 mg) as a brown solid. M. P.: 209-212° C. MS (m/z): 443.2 [M+H]+.

Workup

  1. stirringstirred at rt for 2 h
  2. customfollowed by purification on combiflash
  3. additiona gradient mixture of EtOAc and Petether (7:3) as eluent

Sources & evidence

ORD record
ord-5326653bef4144d8a835a26a640e14ad
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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