Acetyl chloride → HCID 57733004, compound

HRID 1891299Notes

Reaction equation

HRID 1891299 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-e633ec6d248642f0a89c5f7b6c46a0cc
Source dataset
uspto-grants-2013_08
Patent number
US08507524B2

Reaction notes

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