Acetyl chloride → HCID 11691873, compound

HRID 19562Notes

Reaction equation

[CH:1]1([NH:7][C:8]([C:10]2[CH:11]([NH2:34])[C:12]3[C:17]([C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][CH:15]=[C:14]([O:25][CH2:26][CH2:27][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[CH:13]=3)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:35](Cl)(=[O:37])[CH3:36].C(N(CC)CC)C>ClCCl>[CH:1]1([NH:7][C:8]([C:10]2[CH:11]([NH:34][C:35](=[O:37])[CH3:36])[C:12]3[C:17]([C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][CH:15]=[C:14]([O:25][CH2:26][CH2:27][N:28]2[CH2:29][CH2:30][O:31][CH2:32][CH2:33]2)[CH:13]=3)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

1-Amino-6-(2-morpholine-4-yl-ethoxy)-3-phenyl-1H-indene-2-carboxylic acid cyclohexylamide (14 mg, 0.03 mmol) prepared in Example 22 was dissolved in dichloromethane (10 mL), acetyl chloride (24 mg, 0.3 mmol) and triethylamine (30 mg, 0.3 mmol) were added thereto in order at 0° C., and stirred for 24 hrs at RT. The resulting mixture washed with saturated saline and extracted with dichloromethane. The organic layer was separated, dried over anhydrous MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 3 mg of the titled compound (yield: 20%).

Workup

washThe resulting mixture washed with saturated saline
extractionextracted with dichloromethane
customThe organic layer was separated
dry with materialdried over anhydrous MgSO4
concentrationconcentrated under a reduced pressure
customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record: ord-6ade52c437e04e948fb6b338ffa1bb35
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745439B2

Reaction notes

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