2-(Dimethylamino)ethanol → 2-(Dimethylamino)ethyl 3-(3-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)isoquinolin-1-yl)benzoate

HRID 1023404Notes

Reaction equation

HRID 1023404 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].[F:7][C:8]1([F:42])[O:12][C:11]2[CH:13]=[CH:14][C:15]([C:17]3([C:20]([NH:22][C:23]4[N:24]=[C:25]([C:33]5[CH:34]=[C:35]([CH:39]=[CH:40][CH:41]=5)[C:36](Cl)=[O:37])[C:26]5[C:31]([CH:32]=4)=[CH:30][CH:29]=[CH:28][CH:27]=5)=[O:21])[CH2:19][CH2:18]3)=[CH:16][C:10]=2[O:9]1>ClCCl>[F:42][C:8]1([F:7])[O:12][C:11]2[CH:13]=[CH:14][C:15]([C:17]3([C:20]([NH:22][C:23]4[N:24]=[C:25]([C:33]5[CH:34]=[C:35]([CH:39]=[CH:40][CH:41]=5)[C:36]([O:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])=[O:37])[C:26]5[C:31]([CH:32]=4)=[CH:30][CH:29]=[CH:28][CH:27]=5)=[O:21])[CH2:18][CH2:19]3)=[CH:16][C:10]=2[O:9]1

Participants

4

Reactant 2

HCID 79022-(Dimethylamino)ethanolHCID 577330193-(3-(1-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)isoquinolin-1-yl)benzoyl chloride

Product 1

HCID 577330212-(Dimethylamino)ethyl 3-(3-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)isoquinolin-1-yl)benzoateYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To N,N-dimethylethanol amine (921 mg, 1.04 mL, 10.3 mmol) in dichloromethane (5 mL) was added a solution of 3-(3-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)isoquinolin-1-yl)benzoyl chloride in dichloromethane (5 mL). The reaction mixture was stirred at room temperature overnight. The mixture was diluted with DCM (20 mL) and was washed with 1N HCl (20 mL) and saturated NaHCO3 (20 mL). The organics were dried over Na2SO4 and evaporated to yield 2-(dimethylamino)ethyl 3-(3-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)isoquinolin-1-yl)benzoate (1.30 g, 90%). ESI-MS m/z calc. 559.6. found 560.3 (M+1)+. Retention time 1.72 minutes.

Workup

  1. washwas washed with 1N HCl (20 mL) and saturated NaHCO3 (20 mL)
  2. dry with materialThe organics were dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-3757b8de641e46c7b9ee8ca1215f3536
Source dataset
uspto-grants-2014_05
Patent number
US08722704B2

Reaction notes

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