Acetyl chloride → HCID 57733004, compound

HRID 1471846Notes

Reaction equation

HRID 1471846 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-6b71b1e80c3e45c1a7f5bc2b3084d653
Source dataset
uspto-grants-2015_04
Patent number
US09012473B2

Reaction notes

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