HCID 86647994, compound → HCID 68734582, compound

HRID 2383324Notes

Reaction equation

HRID 2383324 reaction equation
CC([CH:5]([CH:9]1[C:18]2[C:13](=[C:14]([C:19]3[N:23]=[C:22]([C:24]4[CH:29]=[CH:28][C:27]([O:30][CH:31]([CH3:33])[CH3:32])=[C:26]([Cl:34])[CH:25]=4)[O:21][N:20]=3)[CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][NH:10]1)[C:6]([O-:8])=[O:7])(C)C>Cl.O1CCOCC1>[ClH:34].[Cl:34][C:26]1[CH:25]=[C:24]([C:22]2[O:21][N:20]=[C:19]([C:14]3[CH:15]=[CH:16][CH:17]=[C:18]4[C:13]=3[CH2:12][CH2:11][NH:10][CH:9]4[CH2:5][C:6]([OH:8])=[O:7])[N:23]=2)[CH:29]=[CH:28][C:27]=1[O:30][CH:31]([CH3:32])[CH3:33]

Participants

4

Reactant 1

HCID 86647994HCID 86647994, compound

Product 1

HCID 68734582HCID 68734582, compoundYield 184.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

1,1-dimethylethyl[5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,3,4-tetrahydro-1-isoquinolinyl]acetate (Preparation 5, 61 mg, 0.126 mmol) was stirred at room temperature for 18 hours in 4M HCl in 1,4-Dioxane (10 mL). Evaporation yielded the title compound (54 mg). 1H NMR (400 MHz, d6-DMSO)) δ 8.19 (1H, s), 8.11 (1H, d), 8.00 (1H, d), 7.61 (1H, d), 7.54 (1H, t), 7.46 (1H, d), 4.96-4.86 (2H, m), 1.37 (6H, d), other aliphatic signals obscured by solvent peaks; m/z (API-ES) 428, 430 [M+H]+.

Workup

  1. customEvaporation

Sources & evidence

ORD record
ord-c199c73e324c4c0fb5e4174afa827b0e
Source dataset
uspto-grants-2012_09
Patent number
US08263620B2

Reaction notes

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