Hydrochloric Acid → HCID 21060089, compound

HRID 228126Notes

Reaction equation

HRID 228126 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:24][C:25]([C@@H:27]2[CH2:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:29][N:28]2C(OC(C)(C)C)=O)=[O:26])[C:10](=[O:23])[N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:13][CH2:12]2)=[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:24][C:25]([C@@H:27]2[CH2:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:29][NH:28]2)=[O:26])[C:10](=[O:23])[N:11]2[CH2:12][CH2:13][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:15][CH2:16]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69078990HCID 69078990, compound

Product 1

HCID 21060089HCID 21060089, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-{(1R)-1-[(4-Chlorophenyl)methyl]-2-oxo-2-(4-(2-pyridyl)piperazinyl)ethyl}((3S)(3-1,2,3,4-tetrahydro-isoquinolyl))carboxamide was prepared according to the procedure used for Preparation XVI using tert-butyl 3-(N-{(1R)-1-[(4-chlorophenyl)methyl]-2-oxo-2-(4-(2-pyridyl)piperazinyl)ethyl}carbamoyl)(3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (Step 2) (450 mg, 0.745 mmol) and 10 mL HCl satd EtOAc. The resulting solid was purified by preparative HPLC (AcOH buffer) and freeze-dried yielding the acetate salt (410 mg). Mass Spec. m/z: 504 (M+H), (ESI, neg. ion) m/z: 502 (M−H). Calc'd for C28H30ClN5O2: 503.21. Anal. Calcd for C28H30ClN5O2—C2H4O2: C, 63.88; H, 6.08; N, 12.42. Found C, 63.66; H, 6.02; N, 12.64.

Workup

  1. customThe resulting solid was purified by preparative HPLC (AcOH buffer)
  2. customfreeze-dried

Sources & evidence

ORD record
ord-10daef7466d84ea5ab6d1aa7b0017b10
Source dataset
uspto-grants-2009_07
Patent number
US07560460B2

Reaction notes

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