Trifluoroacetic acid → HCID 66836156, compound

HRID 2404453Notes

Reaction equation

HRID 2404453 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]([C:29]3[NH:33][C:32]4[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=4[N:30]=3)[O:21][CH:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]3)[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:28][N:25]1[CH2:24][CH2:23][CH:22]([O:21][CH:20]([C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([C:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=3)[CH:15]=2)[C:29]2[NH:30][C:31]3[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=3[N:33]=2)[CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67512697HCID 67512697, compound

Product 1

HCID 66836156HCID 66836156, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)-methyl]phenyl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (407 mg) in dichloromethane (2 mL) is added trifluoroacetic acid (1 mL). After 2 hours at room temperature, volatiles are removed under reduced pressure. The mixture is diluted with water, basified to pH 10 by adding of an aqueous saturated solution of sodium carbonate and extracted with ethyl acetate. The pooled organic extracts are dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 100/0/0 to 85/15/1.5) to afford 2-{(1-methylpiperidin-4-yloxy)[3-(1,2,3,6-tetrahydro-pyridin-4-yl)phenyl]methyl}-1H-benzimidazole.

Workup

  1. customvolatiles are removed under reduced pressure
  2. additionThe mixture is diluted with water
  3. additionby adding of an aqueous saturated solution of sodium carbonate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe pooled organic extracts are dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 100/0/0 to 85/15/1.5)

Sources & evidence

ORD record
ord-3aae3404db6d4cc98b7534530cf10d35
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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