Hydrochloric Acid → HCID 9808720, compound

HRID 228104Notes

Reaction equation

HRID 228104 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:29][C:30]([C@@H:32]2[CH2:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:34][N:33]2C(OC(C)(C)C)=O)=[O:31])[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH2:14][CH2:13]2)=[O:11])=[CH:4][CH:3]=1.Cl>CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:29][C:30]([C@@H:32]2[CH2:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:34][NH:33]2)=[O:31])[C:10]([N:12]2[CH2:13][CH2:14][N:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[NH:24][S:25]([CH3:28])(=[O:26])=[O:27])[CH2:16][CH2:17]2)=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69075325HCID 69075325, compound

Product 1

HCID 9808720HCID 9808720, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following the procedure for the synthesis of Preparation XVI,) N-[(1R)-1-[(4- chlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl]((3S)(3-1,2,3,4-tetrahydroisoquinolyl))carboxamide was prepared from tert-butyl 3-{N-[(1R)-1-[(4-chlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl]carbamoyl}(3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (Step 1) (1.42 g, 2.04 mmol) and 50 mL of EtOAc satd with HCl. The crude product was purified by preparative HPLC (AcOH buffer) yielding the desired product as the acetate salt (250 mg). MS (ESI, pos. ion) m/z: 596 (M+H), (ESI, neg. ion) m/z: 594 (M−H). Calc'd for C30H34ClN5O4S: 595. Anal. Calcd for C30H34ClN5O4S—C2H4O2H2O: C, 57.01; H, 5.98; N, 10.39; Cl, 5.26. Found C, 56.83; H, 6.05; N, 10.25; Cl, 5.25.

Workup

  1. customThe crude product was purified by preparative HPLC (AcOH buffer)

Sources & evidence

ORD record
ord-af975b7f2c214e92a3b1a06845caa600
Source dataset
uspto-grants-2009_07
Patent number
US07560460B2

Reaction notes

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