Cyclopropanesulfonyl chloride → HCID 59275541, compound

HRID 1671890Notes

Reaction equation

HRID 1671890 reaction equation
[CH:1]1([S:4](Cl)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[NH2:8][C:9]1[C:28]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35](=[O:46])[NH:36][C:37]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)([CH3:39])[CH3:38])[CH:30]=2)=[CH:27][C:12]2[C:13]([C:23]([NH:25][CH3:26])=[O:24])=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[O:15][C:11]=2[CH:10]=1>N1C=CC=CC=1>[CH:1]1([S:4]([NH:8][C:9]2[C:28]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35](=[O:46])[NH:36][C:37]([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)([CH3:39])[CH3:38])[CH:30]=3)=[CH:27][C:12]3[C:13]([C:23]([NH:25][CH3:26])=[O:24])=[C:14]([C:16]4[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=4)[O:15][C:11]=3[CH:10]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 2760919Cyclopropanesulfonyl chlorideHCID 59275126HCID 59275126, compound

Product 1

HCID 59275541HCID 59275541, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Cyclopropanesulfonyl chloride (8 μL, 0.058 mmol) was added to a stirring solution of 6-amino-2-(4-fluorophenyl)-N-methyl-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl)benzofuran-3-carboxamide (20 mg, 0.038 mmol) in Pyridine (0.5 mL) at rt. It was allowed to stir for 2 hours. The mixture was concentrated purified by preparative reverse phase HPLC on a C18 column using a suitably buffered H2O/CH3CN gradient, and concentrated to give the titled compound (17 mg, 70%). 1H NMR (500 MHz, CD3OD) δ ppm 8.41 (1H, br. s.), 7.91-8.01 (3H, m), 7.78-7.86 (2H, m), 7.61-7.71 (2H, m), 7.58 (1H, t, J=7.63 Hz), 7.41-7.49 (2H, m), 7.24-7.33 (4H, m), 7.18 (1H, t, J=6.87 Hz), 2.94 (3H, s), 2.34-2.43 (1H, m), 1.77 (6H, s), 0.80-1.03 (4H, m). LC-MS retention time: 1.53 min; m/z (MH+): 626. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters XBridge 5u 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 mm, Rt=15.40 min, purity=99%; Column: Waters Xbridge Phenyl column 4.6×150 mm, 3.5 mm, Rt=12.65 min, purity=99%.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by preparative reverse phase HPLC on a C18 column
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f83e00e6394443279737c2dd0951bfcc
Source dataset
uspto-grants-2011_08
Patent number
US07994171B2

Reaction notes

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