Dichloromethane → HCID 66649325, compound

HRID 418490

Reaction equation

HRID 418490 reaction equation
[C:1]12(CC(O)=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(Cl)Cl.[C:18](Cl)(=[O:22])[C:19](Cl)=O.[NH2:24][C:25]1[C:34]([Cl:35])=[CH:33][CH:32]=[C:31]2[C:26]=1[CH:27]=[CH:28][N:29]([C@H:37]([CH3:41])[C:38]([NH2:40])=[O:39])[C:30]2=[O:36]>CN(C)C=O>[Cl:35][C:34]1[C:25]([NH:24][C:18](=[O:22])[CH2:19][CH:10]2[CH:5]3[CH2:6][CH:7]4[CH2:9][CH:3]([CH2:2][CH:1]2[CH2:8]4)[CH2:4]3)=[C:26]2[C:31](=[CH:32][CH:33]=1)[C:30](=[O:36])[N:29]([C@H:37]([CH3:41])[C:38]([NH2:40])=[O:39])[CH:28]=[CH:27]2

Participants

6

Reactant 4

HCID 6344Dichloromethane3×HCID 65578Oxalyl chlorideHCID 1232211-Adamantaneacetic acidHCID 59515791(R)-2-(5-Amino-6-chloro-1-oxoisoquinolin-2(1H)-yl)propanamide

Product 1

HCID 66649325HCID 66649325, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1-adamantaneacetic acid (600 mg, 0.003 mol) in methylene chloride (5 mL, 0.08 mol) was added oxalyl chloride (0.3 mL, 0.003 mol) and a drop of N,N-dimethylformamide at 0° C. The reaction was stirred at that temperature for 1 h. the solvent was removed under reduced pressureunder reduced pressure and dried under nitrogen. The residue was redissolved in methylene chloride (5 mL, 0.08 mol) and added to a solution of (R)-2-(5-amino-6-chloro-1-oxoisoquinolin-2(1H)-yl)propanamide (420 mg, 0.0016 mol) in methylene chloride (5 mL, 0.08 mol) and N,N-dimethylformamide (2 mL, 0.02 mol), and stirred for 2 hours. the solvent was removed under reduced pressure and the residue was dissolved in 1:3 isopropyl alcohol/chloroform and washed with 1N hydrochloric acid. the solvent was removed under reduced pressure and the residue was purified by flash chromatography to afford the product as an off white solid.

Workup

  1. customat 0° C
  2. customwas removed
  3. customdried under nitrogen
  4. stirringstirred for 2 hours
  5. customthe solvent was removed under reduced pressure
  6. dissolutionthe residue was dissolved in 1:3 isopropyl alcohol/chloroform
  7. washwashed with 1N hydrochloric acid
  8. customthe solvent was removed under reduced pressure
  9. customthe residue was purified by flash chromatography
  10. customto afford the product as an off white solid

Sources & evidence

ORD record
ord-7c58293af81f476286d1e9b21f13d9ec
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Linked notes

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