Acetyl chloride → HCID 57733004, compound

HRID 1023406Notes

Reaction equation

HRID 1023406 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([NH:19][C:20]([C:22]3([C:25]4[CH:35]=[CH:34][C:28]5[O:29][C:30]([F:33])([F:32])[O:31][C:27]=5[CH:26]=4)[CH2:24][CH2:23]3)=[O:21])[N:10]=2)[CH:6]=[CH:7][CH:8]=1.CCN(CC)CC.[C:43](Cl)(=[O:45])[CH3:44]>CN(C=O)C>[C:43]([NH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([NH:19][C:20]([C:22]3([C:25]4[CH:35]=[CH:34][C:28]5[O:29][C:30]([F:33])([F:32])[O:31][C:27]=5[CH:26]=4)[CH2:23][CH2:24]3)=[O:21])[N:10]=2)[CH:6]=[CH:7][CH:8]=1)(=[O:45])[CH3:44]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 57732997HCID 57732997, compound

Product 1

HCID 57733004HCID 57733004, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(1-(3-(aminomethyl)phenyl)isoquinolin-3-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (47 mg, 0.1 mmol) and Et3N (28 μL, 0.2 mmol) in DMF (2 mL) was added acetyl chloride (7.1 μL, 0.1 mmol). The reaction was stirred at room temperature for 10 minutes, then filtered and purified by reverse-phase HPLC to yield the product, N-(1-(3-(acetamidomethyl)phenyl)isoquinolin-3-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide. ESI-MS m/z calc. 515.2. found 516.5 (M+1)+. Retention time 1.97 minutes. 1H NMR (400 MHz, DMSO-d6) δ 9.06 (s, 1H), 8.43-8.40 (m, 2H), 7.98 (d, J=8.2 Hz, 1H), 7.83 (d, J=8.4 Hz, 1H), 7.74-7.70 (m, 1H), 7.61 (d, J=1.1 Hz, 1H), 7.50-7.38 (m, 7H), 4.33 (d, J=6.0 Hz, 2H), 1.85 (s, 3H), 1.57-1.55 (m, 2H), 1.22-1.19 (m, 2H).

Workup

  1. filtrationfiltered
  2. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-ddbc3089c60745408556835841250034
Source dataset
uspto-grants-2014_05
Patent number
US08722704B2

Reaction notes

Loading…