Trifluoroacetic acid → n-{(1r)-1-[(4-Chlorophenyl)methyl]-2-oxo-2-[4-(2-{[(2,4,6-trimethylphenyl)sulfonyl]amino}-phenyl)piperidyl]ethyl}((3s)(3-1,2,3,4-tetrahydroisoquinolyl))carboxamide

HRID 489700Notes

Reaction equation

HRID 489700 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:37][C:38]([C@@H:40]2[CH2:49][C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[CH2:42][N:41]2C(OC(C)(C)C)=O)=[O:39])[C:10](=[O:36])[N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[NH:23][S:24]([C:27]3[C:32]([CH3:33])=[CH:31][C:30]([CH3:34])=[CH:29][C:28]=3[CH3:35])(=[O:26])=[O:25])[CH2:13][CH2:12]2)=[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:37][C:38]([C@@H:40]2[CH2:49][C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[CH2:42][NH:41]2)=[O:39])[C:10](=[O:36])[N:11]2[CH2:12][CH2:13][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[NH:23][S:24]([C:27]3[C:32]([CH3:33])=[CH:31][C:30]([CH3:34])=[CH:29][C:28]=3[CH3:35])(=[O:26])=[O:25])[CH2:15][CH2:16]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23587444Tert-butyl 3-(n-((1r)-1-[(4-chlorophenyl)methyl]-2-oxo-2-[4-(2-{[(2,4,6-trimethylphenyl)sulfonyl]amino}phenyl) piperidyl]ethyl)carbamoyl)(3s)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

Product 1

HCID 10305516n-{(1r)-1-[(4-Chlorophenyl)methyl]-2-oxo-2-[4-(2-{[(2,4,6-trimethylphenyl)sulfonyl]amino}-phenyl)piperidyl]ethyl}((3s)(3-1,2,3,4-tetrahydroisoquinolyl))carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure described in Example 3 (Step b) using tert-butyl 3-(N-((1R)-1-[(4-chlorophenyl)methyl]-2-oxo-2-[4-(2-{[(2,4,6-trimethylphenyl)sulfonyl]amino}phenyl) piperidyl]ethyl)carbamoyl)(3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (Step a) (146 mg, 0.18 mmol) and 50% TFA in CH2Cl2 (10 mL). Purification by reverse phase preparative 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 (81 mg). MS (ESI, pos. ion) m/z: 699 (M+1); (ESI, neg. ion) m/z: 697 (M−1). Calc'd for C30H43ClN4O4S: 698.27.

Workup

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

Sources & evidence

ORD record
ord-3a3aa518323a4b3fb6678a16b3d5dcd7
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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