3,4,5-Trifluorobenzaldehyde → HCID 178505860, compound

HRID 730769Notes

Reaction equation

HRID 730769 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[F:15][C:16]([F:44])([F:43])[C:17]1[CH:41]=[C:40]([NH2:42])[C:20]2[NH:21][C:22]([N:24]3[CH2:29][CH2:28][N:27]([C:30]4[C:35]([C:36]([F:39])([F:38])[F:37])=[CH:34][CH:33]=[CH:32][N:31]=4)[CH2:26][CH2:25]3)=[N:23][C:19]=2[CH:18]=1.[F:45][C:46]1[CH:47]=[C:48]([CH:51]=[C:52]([F:55])[C:53]=1[F:54])[CH:49]=O>C(Cl)(Cl)Cl>[F:45][C:46]1[CH:47]=[C:48]([CH:51]=[C:52]([F:55])[C:53]=1[F:54])[CH2:49][NH:42][C:40]1[C:20]2[NH:21][C:22]([N:24]3[CH2:25][CH2:26][N:27]([C:30]4[C:35]([C:36]([F:37])([F:38])[F:39])=[CH:34][CH:33]=[CH:32][N:31]=4)[CH2:28][CH2:29]3)=[N:23][C:19]=2[CH:18]=[C:17]([C:16]([F:15])([F:43])[F:44])[CH:41]=1

Participants

5

Reactant 3

HCID 27769543,4,5-TrifluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178507663HCID 178507663, compound

Product 1

HCID 178505860HCID 178505860, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

NaBH(OAc)3 (211 mg, 1 mmol, Aldrich) was added to a mixture of 5-(trifluoromethyl)-2-{4-[3-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl}-1H-benzimidazol-7-amine (215 mg, 0.5 mmol, Example 58) and 3,4,5-trifluoro-benzaldehyde (88 mg, 0.55 mmol, Aldrich) in chloroform (2 mL) in one portion. The reaction mixture was stirred at room temperature for 2 h and concentrated in vacuo. The residue was dissolved in EtOAc (30 mL), and washed successively with 1 N NaOH (15 mL) and brine (15 mL), dried over MgSO4, filtered, and the solvent was evaporated in vacuo. The residue was purified by silica gel chromatography, eluting with 25% EtOAc/hexane to give the title compound as a white solid. MS (ESI, pos. ion) m/z: 575 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc (30 mL)
  3. washwashed successively with 1 N NaOH (15 mL) and brine (15 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 25% EtOAc/hexane

Sources & evidence

ORD record
ord-8543e5083038418b86f76039db565e7d
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Reaction notes

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