Trifluoroacetic acid → HCID 23587437, compound

HRID 489672Notes

Reaction equation

HRID 489672 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:28][C:29]([C@@H:31]2[CH2:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:33][N:32]2C(OC(C)(C)C)=O)=[O:30])[C:10](=[O:27])[N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]([F:26])([F:25])[F:24])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.[C:48]([OH:54])([C:50]([F:53])([F:52])[F:51])=[O:49]>C(Cl)Cl>[F:51][C:50]([F:53])([F:52])[C:48]([OH:54])=[O:49].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:28][C:29]([C@@H:31]2[CH2:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:33][NH:32]2)=[O:30])[C:10](=[O:27])[N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]([F:25])([F:24])[F:26])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69151072HCID 69151072, compound

Product 1

HCID 23587437HCID 23587437, compound

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 3-[N-((1R)-1-[(4-chlorophenyl)methyl]-2-oxo-2-{4-[2-(trifluoromethyl)-phenyl]piperidyl}ethyl)-carbamoyl](3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (Step f) (335 mg, 0.5 mmol) and 50% TFA in CH2Cl2 (20 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 solid (202 mg). MS (ESI, pos. ion) m/z: 570 (M+1); (ESI, neg. ion) m/z: 568 (M−1). Calc'd for C31H31ClF3N3O2: 569.21.

Workup

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

Sources & evidence

ORD record
ord-af523cba8d6243f5a203389492e3ea60
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

Loading…