Triethylamine → HCID 59003347, compound

HRID 2267496Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-phenyl-3-(4-piperidinyl)-1H-indole-7-carboxamide (260 mg, 0.8 mmol) in CH2Cl2 at 0° C., triethylamine (0.44 mL, 3.2 mmol) and 2-chloroethylsulfonyl chloride (0.168 mL, 1.6 mmol) were added. The reaction mixture was stirred at 0° C. for 30 min. The reaction mixture was partitioned between CH2Cl2 (100 mL) and water (50 mL). The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (2×100 mL). The combined organic phase washed with brine (50 mL), dried over magnesium sulfate and filtered. The solvent was removed under reduced pressure and purified via filtration through an SPE Cartridge (Aminopropyl NH2, 500 mg/6 mL) to give the title compound (245 mg, 75%).

Workup

customThe reaction mixture was partitioned between CH2Cl2 (100 mL) and water (50 mL)
customThe organic layer was separated
extractionthe aqueous layer was extracted with CH2Cl2 (2×100 mL)
washThe combined organic phase washed with brine (50 mL)
dry with materialdried over magnesium sulfate
filtrationfiltered
customThe solvent was removed under reduced pressure
filtrationpurified via filtration through an SPE Cartridge (Aminopropyl NH2, 500 mg/6 mL)

Sources & evidence

ORD record: ord-e3a05ab4d7f04e5bb3e316ef30e32e23
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858796B2

Reaction notes

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