Dichloromethane → HCID 57411678, compound

HRID 468925Notes

Reaction equation

HRID 468925 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([C:12]1[CH:13]=[C:14]([CH:23]=[CH:24][C:25]=1[CH3:26])[C:15]([NH:17][C:18]1([CH3:22])[CH2:21][CH2:20][CH2:19]1)=[O:16])[CH:6]=2.[Cl:27]CCl.ClN1C(=O)CCC1=O>>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]=1[Cl:27])=[CH:9][CH:8]=[C:7]([C:12]1[CH:13]=[C:14]([CH:23]=[CH:24][C:25]=1[CH3:26])[C:15]([NH:17][C:18]1([CH3:22])[CH2:19][CH2:20][CH2:21]1)=[O:16])[CH:6]=2

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 31398ChlorosuccinimideHCID 67974775HCID 67974775, compound

Product 1

HCID 57411678HCID 57411678, compoundYield 32%

Procedure

A solution of 3-(3-aminoisoquinolin-7-yl)-4-methyl-N-(1-methylcyclobutyl)benzamide (50.0 mg; 0.145 mmol) in dichloromethane (3 mL; 46.80 mmol) was treated with N-chlorosuccinimide (27.9 mg; 0.209 mmol). The reaction mixture was stirred at room temperature for 7 hours. The crude reaction mixture was filtered through a plug of silica gel, which was rinsed with ethyl acetate. The filtrate was evaporated in vacuo and the resulting residue was purified via preparatory reverse-phase HPLC and lyophilized to yield 17.3 mg (32%) of the title compound. LCMS (ESI): RT (min)=5.078, M+H=380.2, method=E; 1H NMR (400 MHz, DMSO) δ 8.92 (s, 1H), 8.35 (s, 1H), 7.94 (s, 1H), 7.86 (d, J=8.8 Hz, 1H), 7.80 (s, 1H), 7.78 (d, J=8.0 Hz, 1H), 7.72 (d, J=8.9 Hz, 1H), 7.40 (d, J=7.9 Hz, 1H), 6.36 (s, 2H), 2.39-2.32 (m, 2H), 2.31 (s, 3H), 2.02-1.93 (m, 2H), 1.86-1.75 (m, 2H), 1.47 (s, 3H).

Workup

  1. customThe crude reaction mixture
  2. filtrationwas filtered through a plug of silica gel, which
  3. washwas rinsed with ethyl acetate
  4. customThe filtrate was evaporated in vacuo
  5. customthe resulting residue was purified via preparatory reverse-phase HPLC

Sources & evidence

ORD record
ord-c8431e5e7f014024ab3fb0f70b6e2cd5
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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