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

HRID 228108Notes

Reaction equation

HRID 228108 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[N: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.Cl>CCOC(C)=O>[NH2:8][CH2:9][CH2:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N: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 313Hydrochloric AcidHCID 69073578tert-butyl 3-[N-((1R)-2-{4-[2-({2-[(tert-butoxy) carbonylamino]ethyl}amino)phenyl]piperazinyl}-1-[(4-chlorophenyl)methyl]-2-oxoethyl)carbamoyl](3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

Product 1

HCID 10166491n-[(1r)-2-(4-{2-[(2-Aminoethyl)amino]phenyl}piperazinyl)-1-[(4-chlorophenyl)methyl]-2-oxoethyl]((3s)(3-1,2,3,4-tetrahydroisoquinolyl))carboxamideYield 89.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-[(1R)-2-(4-(2-[(2-aminoethyl)amino]phenyl)piperazinyl)-1-[(4-chlorophenyl)methyl]-2-oxoethyl] ((3S)(3-1,2,3,4-tetrahydroisoquinolyl))carboxamide was prepared according to Preparation XVI using tert-butyl 3-[N-((1R)-2-{4-[2-({2-[(tert-butoxy)carbonylamino]-ethyl}amino)phenyl]-piperazinyl}-1-[(4-chlorophenyl)-methyl]-2-oxoethyl)-carbamoyl](3S)-1,2,3,4-tetrahydro-isoquinoline-2-carboxylate (150 mg, 0.18 mmol) and 25 mL of EtOAc satd with HCl. The crude product was concentrated to provide the desired product (90 mg). MS (ESI, pos. ion) m/z: 561 (M+H), (ESI, neg. ion) m/z: 559 (M−H). Calc'd for C31H37ClN6O2: 560.27.

Workup

  1. customN-[(1R)-2-(4-(2-[(2-aminoethyl)amino]phenyl)piperazinyl)-1-[(4-chlorophenyl)methyl]-2-oxoethyl] ((3S)(3-1,2,3,4-tetrahydroisoquinolyl))carboxamide was prepared
  2. concentrationThe crude product was concentrated

Sources & evidence

ORD record
ord-515a7c9aa23a49b9babed966217a36c0
Source dataset
uspto-grants-2009_07
Patent number
US07560460B2

Reaction notes

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