Acetic Acid → HCID 178482053, compound

HRID 1189675Notes

Reaction equation

HRID 1189675 reaction equation
[F:1][C:2]([F:47])([F:46])[C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10]([C:12]2[C:38]([N:39]([CH3:45])[CH:40]3[CH2:44][CH2:43][S:42][CH2:41]3)=[CH:37][C:15]3[N:16]([CH3:36])[C:17]([NH:19][C:20]4[C:25]([Cl:26])=[CH:24][CH:23]=[C:22]([CH2:27][NH:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[C:21]=4[Cl:35])=[N:18][C:14]=3[CH:13]=2)=[O:11])[CH2:5][CH2:4]1.C1C=C(Cl)C=C(C(OO)=[O:56])C=1.C(Cl)Cl.C(O)(=O)C>C([O-])(O)=O.[Na+]>[F:47][C:2]([F:1])([F:46])[C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10]([C:12]2[C:38]([N:39]([CH3:45])[CH:40]3[CH2:44][CH2:43][S:42](=[O:56])[CH2:41]3)=[CH:37][C:15]3[N:16]([CH3:36])[C:17]([NH:19][C:20]4[C:25]([Cl:26])=[CH:24][CH:23]=[C:22]([CH2:27][NH:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:31])[CH3:32])[C:21]=4[Cl:35])=[N:18][C:14]=3[CH:13]=2)=[O:11])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 178482052HCID 178482052, compound2×

Product 1

HCID 178482053HCID 178482053, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of N-(trans-4-trifluoromethyl-cyclohexyl)-2-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-[N-methyl-N-(tetrahydro-thiophen-3-yl)-amino]-1-methyl-1H-benzimidazole-5-carboxylic acid amide (compound 117, 70 mg, 0.098 mmol), mCPBA (23 mg, ˜0.10 mmol), DCM (5 mL) and glacial acetic acid (0.5 mL) is stirred for 2.5 h at rt. The mixture is diluted with sat aq NaHCO3, extracted with EtOAc, the combined organic phases are dried with Na2SO4, filtered and concentrated.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialthe combined organic phases are dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2174fc5ff51043a1af435030dc32948b
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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