Hydrochloric Acid → HCID 69156420, compound

HRID 750346Notes

Reaction equation

HRID 750346 reaction equation
C[O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([Cl:20])[CH:18]=3)[C:13](=[O:21])[N:12]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=3)[C:11]=2[C:33](=[O:36])[CH2:34][CH3:35])=[CH:6][CH:5]=1.[OH-].[Na+].Cl>CO>[Cl:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:21])[N:12]([CH2:22][C:23]1[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:28]=1)[C:11]([C:33](=[O:36])[CH2:34][CH3:35])=[C:10]2[C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:37])=[O:2])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69156846HCID 69156846, compound

Product 1

HCID 69156420HCID 69156420, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution (2.0 ml) of 4-[6-chloro-2-(4-methanesulfonylbenzyl)-1-oxo-3-propionyl-1,2-dihydroisoquinolin-4-yl]benzoic acid methyl ester (100 mg) in methanol was added 1N sodium hydroxide (0.28 ml) at room temperature with stirring, and the mixture was stirred for 18 hrs. at the same temperature. The reaction mixture was neutralized with 1N hydrochloric acid and concentrated under reduced pressure. The residue was purified by preparative HPLC, and crystallized from methanol to give the title compound (42 mg) in beige crystals. 1H NMR (CDCl3) δ: 0.56 (3H, t, J=6.9 Hz), 1.79 (2H, q, J=6.9 Hz), 3.02 (3H, s), 5.36 (2H, s), 7.22 (1H, d, J=2.1 Hz), 7.40-7.49 (4H, m), 7.56 (1H, dd, J=2.1, 8.7 Hz), 7.91 (2H, d, J=8.7 Hz), 8.24 (2H, d, J=8.7 Hz), 8.50 (1H, d, J=8.7 Hz). HPLC analysis: purity 99.9% (retention time: 3.92 min). MS (ESI+): 524.0 (M+H), 526.0.

Workup

  1. stirringthe mixture was stirred for 18 hrs
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by preparative HPLC
  4. customcrystallized from methanol

Sources & evidence

ORD record
ord-1fbb5f88e8c347a6919a8806b1380703
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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