3-Methoxypropyl-6-[(tetrahydro-2H-pyran-2-yloxy)carbamoyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate → 3-Methoxypropyl-6-(hydroxycarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 2036860Notes

Reaction equation

HRID 2036860 reaction equation
O1CCCCC1[O:7][NH:8][C:9]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH2:17][N:16]([C:21]([O:23][CH2:24][CH2:25][CH2:26][O:27][CH3:28])=[O:22])[CH2:15][CH2:14]2)=[O:10]>CO.Cl>[CH3:28][O:27][CH2:26][CH2:25][CH2:24][O:23][C:21]([N:16]1[CH2:15][CH2:14][C:13]2[C:18](=[CH:19][CH:20]=[C:11]([C:9](=[O:10])[NH:8][OH:7])[CH:12]=2)[CH2:17]1)=[O:22]

Participants

4

Reactant 1

HCID 866565953-Methoxypropyl-6-[(tetrahydro-2H-pyran-2-yloxy)carbamoyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 442303933-Methoxypropyl-6-(hydroxycarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylateYield 101%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 90 mg 3-methoxypropyl 6-[(tetrahydro-2H-pyran-2-yloxy)carbamoyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate in 1 ml methanol and 1.5 ml aqueous HCl (0.1 N) is stirred for 3 h at ambient temperature. The reaction mixture is lyophilized. 71.4 mg of a colorless solid are obtained. MH+=309.0

Sources & evidence

ORD record
ord-a92f466b08c74a34b4db56d7292c8fab
Source dataset
uspto-grants-2013_11
Patent number
US08575193B2

Reaction notes

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