Acetyl chloride → HCID 59275467, compound

HRID 1025079Notes

Reaction equation

HRID 1025079 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]([C:18]([NH:20][CH3:21])=[O:19])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28](=[O:39])[NH:29][C:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([CH3:32])[CH3:31])[CH:23]=1.[C:40](Cl)(=[O:42])[CH3:41]>N1C=CC=CC=1>[C:40]([NH:1][C:2]1[C:7]2[C:8]([C:18]([NH:20][CH3:21])=[O:19])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28](=[O:39])[NH:29][C:30]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)([CH3:32])[CH3:31])[CH:23]=1)(=[O:42])[CH3:41]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 59275296HCID 59275296, compound

Product 1

HCID 59275467HCID 59275467, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-amino-2-(4-fluorophenyl)-N-methyl-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl)benzofuran-3-carboxamide (20 mg, 0.038 mmol) was diluted in pyridine (1 mL) and treated with excess acetyl chloride (10 μL). The reaction was allowed to stir for 2 hours. The mixture was concentrated and diluted with MeOH (1 mL). The product began to crash out, it was sonicated and filtered and washed with MeOH to afford the titled compound (8 mg, 34%). 1H NMR (500 MHz, DMSO-d6) δ ppm 9.41 (1 H, s), 8.43 (1 H, s), 8.31-8.38 (1 H, m), 7.88-7.92 (1 H, m), 7.82-7.87 (2 H, m), 7.80 (1 H, d, J=7.63 Hz), 7.71 (1 H, d, J=8.55 Hz), 7.54-7.60 (1 H, m), 7.43-7.49 (2 H, m), 7.36-7.43 (5 H, m), 7.28 (2 H, t, J=7.78 Hz), 7.17 (1 H, t, J=7.32 Hz), 2.76 (3 H, d), 1.79 (3 H, s), 1.69 (6 H, s). LC-MS retention time 1.42 min; m/z 564 (MH+). LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters XBridge 5 u C18 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 5% acetonitrile/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% acetonitrile/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode. Additional HPLC method: Solvent A=5% CH3CN/95% H2O/0.1% TFA, Solvent B=95% CH3CN/5% H2O/0.1% TFA, Start % B=10, Final % B=100, Gradient time=15 min, Stop time=18 min, Flow Rate=1 ml/min. Column: Waters Sunfire C-18, 4.6×150 mm, 3.5 μm, Rt=12.00 min, purity=96%; Column: Waters Xbridge Phenyl column 4 6×150 mm, 3.5 μm, Rt=11.26 min, purity=95%.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with MeOH (1 mL)
  3. customit was sonicated
  4. filtrationfiltered
  5. washwashed with MeOH

Sources & evidence

ORD record
ord-8c46a74ca0104a6b88863d5891e4837a
Source dataset
uspto-grants-2014_05
Patent number
US08722688B2

Reaction notes

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