Methanol → HCID 11639452, compound

HRID 506984Notes

Reaction equation

HRID 506984 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:35])=[C:11]([N:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][C:17]([O:23][CH2:24][CH2:25][NH:26]C(=O)OC(C)(C)C)=[CH:18][CH:19]=4)[C:14]3=[O:34])[CH:12]=2)=[O:6])[CH2:3][CH2:2]1.CO>Cl.O1CCOCC1>[NH2:26][CH2:25][CH2:24][O:23][C:17]1[CH:16]=[C:15]2[C:20]([CH:21]=[CH:22][N:13]([C:11]3[CH:12]=[C:7]([CH:8]=[CH:9][C:10]=3[CH3:35])[C:5]([NH:4][CH:1]3[CH2:3][CH2:2]3)=[O:6])[C:14]2=[O:34])=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 86620855HCID 86620855, compound

Product 1

HCID 11639452HCID 11639452, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl {2-[(2-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-1-oxo-1,2-dihydroisoquinolin-7-yl)oxy]ethyl}carbamate (145 mg) was dissolved in 4N HCl in dioxane (1.2 ml) and methanol (0.9 ml) stirred at room temperature for 18 hours. The orange solution was concentrated and purified by column chromatography on an ion exchange column (isolute SCX column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK) using initially methanol and then a 99:1 mixture of methanol and aqueous ammonia solution to give 3-[7-(2-aminoethoxy)-1-oxoisoquinolin-2(1H)-yl]-N-cyclopropyl-4-methylbenzamide as a white solid (102 mg); NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.69 (m, 2H), 2.10 (s, 3H), 2.22 (s, 2H), 2.86 (m, 1H), 2.94 (t, 2H), 4.05 (m, 2H), 6.73 (d, 1H), 7.22 (d, 1H), 7.43 (m, 1H), 7.50 (d, 1H), 7.66 (d, 1H), 7.72 (d, 1H), 7.76 (d, 1H), 7.87 (m, 1H), 8.46 (d, 1H); Mass Spectrum: M+H+ 378.

Workup

  1. concentrationThe orange solution was concentrated
  2. custompurified by column chromatography on an ion exchange column (isolute SCX column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK)
  3. additiona 99:1 mixture of methanol and aqueous ammonia solution

Sources & evidence

ORD record
ord-3ac4c9e8e82441608e6072d44712c09c
Source dataset
uspto-grants-2010_08
Patent number
US07786115B2

Reaction notes

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