Hydrochloric Acid → [2-(4-((2R)-2-[((3S)(3-1,2,3,4-Tetrahydroisoquinolyl))carbonylamino]-3-(4-chlorophenyl)propanoyl}piperazinyl)phenyl]-N,N-dimethylcarboxamide

HRID 1242765Notes

Reaction equation

HRID 1242765 reaction equation
[CH3:1][N:2]([CH3:48])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:47])[C@H:18]([NH:27][C:28]([C@@H:30]2[CH2:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:32][N:31]2C(OC(C)(C)C)=O)=[O:29])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[CH2:13][CH2:12]1)=[O:4].Cl>CCOC(C)=O>[CH2:32]1[C:33]2[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:39][C@@H:30]([C:28]([NH:27][C@H:18]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[C:17]([N:14]2[CH2:13][CH2:12][N:11]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[C:3]([N:2]([CH3:1])[CH3:48])=[O:4])[CH2:16][CH2:15]2)=[O:47])=[O:29])[NH:31]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69072944Tert-butyl 3-[n-((1r)-2-{4-[2-(n,n-dimethylcarbamoyl)-phenyl]piperazinyl}-1-[(4-chlorophenyl)methyl]-2-oxoethyl)carbamoyl](3s)-1,2,3,4-tetrahydro-isoquinoline-2-carboxylate

Product 1

HCID 10144701[2-(4-((2R)-2-[((3S)(3-1,2,3,4-Tetrahydroisoquinolyl))carbonylamino]-3-(4-chlorophenyl)propanoyl}piperazinyl)phenyl]-N,N-dimethylcarboxamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

[2-(4-{(2R)-2-[((3S)(3-1,2,3,4-Tetrahydro-isoquinolyl))carbonylamino]-3-(4-chlorophenyl)-propanoyl}piperazinyl)phenyl]-N,N-dimethylcarboxamide was prepared according to the procedure described in Preparation XVI by using tert-butyl 3-[N-((1R)-2-{4-[2-(N,N-dimethylcarbamoyl)-phenyl]piperazinyl}-1-[(4-chlorophenyl)methyl]-2-oxoethyl)carbamoyl](3S)-1,2,3,4-tetrahydro-isoquinoline-2-carboxylate (Step 6) (156 mg, 0.23 mmol) and a satd soln of HCl in EtOAc (5 mL). The title compound was isolated by filtration as a white solid, and purified by preparative HPLC (TFA buffer) (125 mg). MS (ESI, pos.ion) m/z: 574 (M+H). Calc'd for C32H36ClN5O3: 573.25.

Workup

  1. custom[2-(4-{(2R)-2-[((3S)(3-1,2,3,4-Tetrahydro-isoquinolyl))carbonylamino]-3-(4-chlorophenyl)-propanoyl}piperazinyl)phenyl]-N,N-dimethylcarboxamide was prepared

Sources & evidence

ORD record
ord-b68e63faa5234cd7bcca97b365847285
Source dataset
uspto-grants-2006_10
Patent number
US07115607B2

Reaction notes

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