Trifluoroacetic acid → HCID 67173930, compound

HRID 41106

Reaction equation

HRID 41106 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8](=[O:11])[NH:9][CH3:10])[CH:5]=[C:4]([F:12])[C:3]=1[C:13]1[N:17]([CH2:18][C@H:19]2[O:24][CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20]2)[C:16]2[CH:32]=[CH:33][C:34]([CH3:36])=[CH:35][C:15]=2[N:14]=1.[C:37]([OH:43])([C:39]([F:42])([F:41])[F:40])=[O:38]>C(Cl)Cl>[F:40][C:39]([F:42])([F:41])[C:37]([OH:43])=[O:38].[F:12][C:4]1[CH:5]=[C:6]([CH:7]=[C:2]([F:1])[C:3]=1[C:13]1[N:17]([CH2:18][C@H:19]2[O:24][CH2:23][CH2:22][NH:21][CH2:20]2)[C:16]2[CH:32]=[CH:33][C:34]([CH3:36])=[CH:35][C:15]=2[N:14]=1)[C:8]([NH:9][CH3:10])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67173392(R)-tert-butyl 2-((2-(2,6-difluoro-4-(methylcarbamoyl)phenyl)-5-methyl-1H-benzo[d]imidazol-1-yl)methyl)morpholine-4-carboxylate

Product 1

HCID 67173930HCID 67173930, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-tert-butyl 2-((2-(2,6-difluoro-4-(methylcarbamoyl)phenyl)-5-methyl-1H-benzo[d]imidazol-1-yl)methyl)morpholine-4-carboxylate (770 mg, 1.54 mmol) was dissolved in DCM (10.0 mL). Afterward, TFA (2.00 mL) was added to the mixture at 0° C. The resulting mixture was stirred at room temperature for 1 hr and then concentrated under reduced pressure. The crude (S)-3,5-difluoro-N-methyl-4-(5-methyl-1-(morpholin-2-ylmethyl)-1H-benzo[d]imidazol-2-yl)benzamide trifluoroacetic acid salt product was used without further purification (790 mg) in the next step. It was analyzed on analytical HPLC MS using the high pH gradient method (mobile phase: 5-95% B; A: H2O with 10 mM NH4CO3 and 0.375% NH4OH v/v; B: CH3CN; 2.25 min run; X-Bridge C18; column size: 2.1×30 mm; particle size: 5 μm). MS m/z 401.3 [M+H]+ (ESI), Rt 1.37 min.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude (S)-3,5-difluoro-N-methyl-4-(5-methyl-1-(morpholin-2-ylmethyl)-1H-benzo[d]imidazol-2-yl)benzamide trifluoroacetic acid salt product was used without further purification (790 mg) in the next step
  3. custom2.25 min

Sources & evidence

ORD record
ord-0ca3b92738254c9b985b4ed3fbde0798
Source dataset
uspto-grants-2013_09
Patent number
US08530467B2

Linked notes

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