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

HRID 489708Notes

Reaction equation

HRID 489708 reaction equation
C(OC([NH:8][CH2:9][CH2:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]1[CH2:23][CH2:22][N:21]([C:24](=[O:54])[C@H:25]([NH:34][C:35]([C@@H:37]2[CH2:46][C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH2:39][N:38]2C(OC(C)(C)C)=O)=[O:36])[CH2:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[CH2:20][CH2:19]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH2:9][CH2:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]1[CH2:19][CH2:20][N:21]([C:24](=[O:54])[C@H:25]([NH:34][C:35]([C@@H:37]2[CH2:46][C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH2:39][NH:38]2)=[O:36])[CH2:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69151293tert-Butyl 3-[N-((1R)-2-{4-[2-({2-[(tert-butoxy)carbonylamino]ethyl}-amino)phenyl]-piperidyl}-1-[(4-chlorophenyl)methyl]-2-oxoethyl)carbamoyl](3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

Product 1

HCID 10187843n-[(1r)-2-(4-{2-[(2-Aminoethyl)amino]phenyl}piperidyl)-1-[(4-chlorophenyl)methyl]-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)-2-{4-[2-({2-[(tert-butoxy)carbonyl-amino]ethyl}-amino)phenyl]-piperidyl}-1-[(4-chlorophenyl)methyl]-2-oxoethyl)carbamoyl](3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (Step a) (386 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 foam (162 mg). MS (ESI, pos. ion) m/z: 560 (M+1); (ESI, neg. ion) m/z: 558 (M−1). Calc'd for C32H38ClN5O2: 559.27. Anal. Calcd for C32H38ClN5O2-3C2HF3O2: C, 50.59; H, 4.58; N, 7.76. Found: C, 50.98; H, 4.87; N, 8.01.

Workup

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

Sources & evidence

ORD record
ord-c49765abd7c5437a9937a9f327046056
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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