Trifluoroacetic acid → N-[(1R)-1-[(4-Chlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperidyl)-2-oxoethyl]-2-(4-piperidyl)acetamide

HRID 489658Notes

Reaction equation

HRID 489658 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:29][C:30]([CH2:32][CH:33]2[CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35][CH2:34]2)=[O:31])[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH2:14][CH2:13]2)=[O:11])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:29][C:30](=[O:31])[CH2:32][CH:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[NH:24][S:25]([CH3:28])(=[O:26])=[O:27])[CH2:14][CH2:13]2)=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69150963HCID 69150963, compound

Product 1

HCID 10303132N-[(1R)-1-[(4-Chlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperidyl)-2-oxoethyl]-2-(4-piperidyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure described in Example 3, Step (b) from tert-butyl 4-({N-[(1R)-1-[(4-chlorophenyl)methyl]-2-(4-(2-[(methylsulfonyl)-amino]phenyl}piperidyl)-2-oxoethyl]-carbamoyl)methyl)-piperidinecarboxylate (Step a) (330 mg, 0.5 mmol) and 50% TFA in CH2Cl2 (20 mL). Purification by preparative reverse phase HPLC [Phenomenex; 5 μm 250×21.2 mm, 5% to 95% CH3CN (0.1% TFA) in H2O (0.1% TFA) over 30 min, then 100% CH3CN (0.1% TFA) for 2 min] provided the title compound (TFA salt) as a white foam (242 mg). MS (EST, pos. ion) m/z: 561 (M+1); (ESI, neg. ion) m/z: 559 (M−1). Calc'd for C28H37ClN4O4S: 560.22. Anal. Calcd for C28H37ClN4O4S.1.6C2HF3O2: C, 50.40; H, 5.23; N, 7.53. Found: C, 50.54; H, 5.53; N, 7.75.

Workup

  1. customThe title compound was prepared
  2. customPurification by preparative reverse phase HPLC [Phenomenex

Sources & evidence

ORD record
ord-33b5d3c1b56e4ba487dcca550149d894
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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