Trifluoroacetic acid → HCID 66810863, compound

HRID 1486776Notes

Reaction equation

HRID 1486776 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([CH2:21][NH:22][C:23]([C:25]3[C:33]4[N:32]=[C:31]([C:34]([CH3:37])([CH3:36])[CH3:35])[NH:30][C:29]=4[CH:28]=[CH:27][CH:26]=3)=[O:24])[CH2:17][CH2:16]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH:8]1[CH2:9][CH2:10][CH:11]([CH2:14][N:15]2[CH2:16][CH2:17][CH:18]([CH2:21][NH:22][C:23]([C:25]3[C:33]4[N:32]=[C:31]([C:34]([CH3:37])([CH3:36])[CH3:35])[NH:30][C:29]=4[CH:28]=[CH:27][CH:26]=3)=[O:24])[CH2:19][CH2:20]2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66810908HCID 66810908, compound

Product 1

HCID 66810863HCID 66810863, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude 4-(4-{[(2-tert-butyl-1H-benzoimidazole-4-carbonyl)amino]methyl}-piperidin-1-ylmethyl)piperidine-1-carboxylic acid tert-butyl ester, prepared as in the previous step (5.1 g, 10 mmol) was treated with a mixture of trifluoroacetic acid (40 mL) and dichloromethane (40 mL) at room temperature for 0.5 h. The mixture was concentrated in vacuo, redissolved in dichloromethane (25 mL) and basified with 1M aqueous sodium hydroxide (15 mL). The organic layer was removed, and the aqueous layer re-extracted with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered, and concentrated in vacuo to afford the desired product as a brown foam (3.6 g, 8.8 mmol, 88%). (m/z): [M+H]+ calcd for C24H37N5O, 412.31. found 412.6.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionredissolved in dichloromethane (25 mL)
  3. customThe organic layer was removed
  4. extractionthe aqueous layer re-extracted with dichloromethane
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9d62a786fc6c44fa82189841ae148d18
Source dataset
uspto-grants-2016_08
Patent number
US09428489B2

Reaction notes

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