Hydrochloric Acid → HCID 67203504, compound

HRID 85176Notes

Reaction equation

HRID 85176 reaction equation
CC1(C)[O:6][C@H:5]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([NH:15][C:16]([C:18]3[C:26]4[N:25]=[C:24]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[C:33]([F:36])([F:35])[F:34])[NH:23][C:22]=4[CH:21]=[CH:20][CH:19]=3)=[O:17])[CH:12]=[CH:13][CH:14]=2)[CH2:4][O:3]1.Cl>C1COCC1.CO>[OH:6][C@@H:5]([CH2:4][OH:3])[CH2:7][O:8][C:9]1[CH:10]=[C:11]([NH:15][C:16]([C:18]2[C:26]3[N:25]=[C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:33]([F:35])([F:36])[F:34])[NH:23][C:22]=3[CH:21]=[CH:20][CH:19]=2)=[O:17])[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67203479(R)-N-(3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxamide

Product 1

HCID 67203504HCID 67203504, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-N-(3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxamide (134; 51.5 mg, 0.1 mmol) in 3 mL of THF was added 4 N HCl dropwise until observe color change, solution darkens, at which point an additional 1 mL of HCL is added and the solution is allowed to stir at room temperature for 18 h. The reaction mixture was diluted with MeOH and then concentrated under reduced pressure. The resulting yellowish suspension is purified by preparatory HPLC. The desired product (Compound 725) was obtained as a white solid (32.5 mg, 64%). MS (ESI) calcd for C24H20F3N3O4: 471.14; found: 472 [M+H].

Workup

  1. additionat which point an additional 1 mL of HCL is added
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting yellowish suspension is purified by preparatory HPLC

Sources & evidence

ORD record
ord-aed6808809394ee3b5a5e39949229bfe
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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