Water → HCID 66835964, compound

HRID 572858Notes

Reaction equation

HRID 572858 reaction equation
C(OC([NH:8][CH2:9][CH2:10][S:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]([C:27]2[NH:31][C:30]3[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=3[N:28]=2)[O:19][CH:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]2)[CH:13]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.O.[OH-].[Na+]>ClCCl>[NH:28]1[C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=[C:27]1[CH:18]([O:19][CH:20]1[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]1)[C:14]1[CH:13]=[C:12]([S:11][CH2:10][CH2:9][NH2:8])[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 67513106HCID 67513106, compound

Product 1

HCID 66835964HCID 66835964, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-tert-butoxycarbonyl-2-{3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)methyl]phenylsulfanyl}ethylamine in dichloromethane (2 mL) is added trifluoroacetic acid (0.5 ml) at room temperature. The mixture is stirred at room temperature for 24 h. Water is added and the mixture is basified by adding a solution of sodium hydroxide. The aqueous phase is extracted by ethyl acetate. The organic phase is washed by water, then dried over magnesium sulfate and concentrated. The residue is triturated in diisopropylether to give 2-{3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)methyl]phenylsulfanyl}ethylamine.

Workup

  1. extractionThe aqueous phase is extracted by ethyl acetate
  2. washThe organic phase is washed by water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue is triturated in diisopropylether

Sources & evidence

ORD record
ord-d0f235bc352c43b4aa42d2c60cd6f7ec
Source dataset
uspto-grants-2015_05
Patent number
US09029357B2

Reaction notes

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