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Hydrochloric Acid → N-Cyclopropyl-3-(2-(cyclopropylmethyl)-4-((2-(dimethylamino)ethoxy)methyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-4-methylbenzamide

HRID 907330
Notes
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Reaction equation

HRID 907330 reaction equation
[CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[N:18]([CH2:24][CH:25]3[CH2:27][CH2:26]3)[CH:17]=[C:16]4[CH2:28][OH:29])[CH:7]=2)[CH2:3][CH2:2]1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[CH3:46][N:47]([CH3:51])[CH2:48][CH2:49]O.Cl>ClCCl.O1CCOCC1>[CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[N:18]([CH2:24][CH:25]3[CH2:26][CH2:27]3)[CH:17]=[C:16]4[CH2:28][O:29][CH2:49][CH2:48][N:47]([CH3:51])[CH3:46])[CH:7]=2)[CH2:2][CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 79022-(Dimethylamino)ethanol2×HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-2×HCID 57551835HCID 57551835, compound

Product 1

HCID 57551726N-Cyclopropyl-3-(2-(cyclopropylmethyl)-4-((2-(dimethylamino)ethoxy)methyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-4-methylbenzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of the product of step i) (130 mg) in dichloromethane (5 mL) was treated with (−/+)-10-camphorsulfonic acid (680 mg) and N,N-dimethylethanolamine (0.32 mL) and stirred at room temperature for 17 hours. 4N Hydrogen chloride in 1,4-dioxane (0.85 mL) was added and the reaction was stirred at room temperature for 6 hrs. Additional N,N-dimethylethanolamine (0.33 mL), (−/+)-10-camphorsulfonic acid (680 mg) and 4N hydrogen chloride in 1,4-dioxane (0.9 mL) were added and the reaction was stirred at room temperature for 60 hours. The reaction mixture was diluted with dichloromethane (100 mL) and washed with saturated sodium bicarbonate (100 mL) solution. The organics were evaporated in vacuo, and the crude product was purified by HPLC to yield the title compound as a solid (25.0 mg).

Workup

  1. stirringthe reaction was stirred at room temperature for 6 hrs
  2. stirringthe reaction was stirred at room temperature for 60 hours
  3. washwashed with saturated sodium bicarbonate (100 mL) solution
  4. customThe organics were evaporated in vacuo
  5. customthe crude product was purified by HPLC

Sources & evidence

ORD record
ord-418a1ea5769047d79af4b6f74816bb9b
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08012979B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes