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

HRID 489698Notes

Reaction equation

HRID 489698 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:36][C:37]([C@@H:39]2[CH2:48][C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH2:41][N:40]2C(OC(C)(C)C)=O)=[O:38])[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]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]#[N:35])(=[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:36][C:37]([C@@H:39]2[CH2:48][C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH2:41][NH:40]2)=[O:38])[C:10]([N:12]2[CH2:13][CH2:14][CH:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[NH:24][S:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]#[N:35])(=[O:26])=[O:27])[CH2:16][CH2:17]2)=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69151038Tert-butyl 3-(n-{(1r)-1-[(4-chlorophenyl)methyl]-2-[4-(2-{[(2-cyanophenyl)sulfonyl]amino}phenyl)piperidyl]-2-oxoethyl}carbamoyl)(3s)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

Product 1

HCID 10122668n-{(1r)-1-[(4-Chlorophenyl)methyl]-2-[4-(2-{[(2-cyanophenyl)sulfonyl]amino}-phenyl)piperidyl]-2-oxoethyl}((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-[4-(2-{[(2-cyanophenyl}sulfonyl]amino}phenyl)piperidyl]-2-oxoethyl]carbamoyl)(3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (Step a) (167 mg, 0.21 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 (76 mg). MS (ESI, pos. ion) m/z: 682 (M+1); (ESI, neg. ion) m/z: 680 (M−1). Calc'd for C37H36ClN5O4S: 681.22.

Workup

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

Sources & evidence

ORD record
ord-38bf3b8403434c93845969ea469f29b6
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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