HCID 67202506, compound → HCID 58278944, compound

HRID 85183Notes

Reaction equation

HRID 85183 reaction equation
[F:1][CH:2]([F:37])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[NH:13][C:12]2[CH:14]=[C:15]([F:36])[CH:16]=[C:17]([C:18]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][C@H:29]4[CH2:33][O:32]C(C)(C)[O:30]4)[CH:22]=3)=[O:19])[C:11]=2[N:10]=1>Cl.CO>[F:37][CH:2]([F:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[NH:13][C:12]2[CH:14]=[C:15]([F:36])[CH:16]=[C:17]([C:18]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][C@H:29]([OH:30])[CH2:33][OH:32])[CH:22]=3)=[O:19])[C:11]=2[N:10]=1

Participants

4

Reactant 1

HCID 67202506HCID 67202506, compound

Product 1

HCID 58278944HCID 58278944, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

Ten drops of concentrated HCl were added to a solution of (S)-2-(2-(difluoromethyl)phenyl)-N-(3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-6-fluoro-1H-benzo[d]imidazole-4-carboxamide (147; 200 mg, 0.391 mmol) in methanol (15 mL). The resulting reaction mixture was stirred at room temperature for 2 h and then concentrated under reduced pressure to afford (R)-2-(2-(difluoromethyl)phenyl)-N-(3-(2,3-dihydroxypropoxy)phenyl)-6-fluoro-1H-benzo[d]imidazole-4-carboxamide (Compound 811) (160 mg, 87%). MS (ESI) calcd for C27H24F3N3O4: 511.17; found: 512 [M+H].

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9a7f7235cb844e8fa0b9706c0ebe8afc
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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