Triethylamine → HCID 86615469, compound

HRID 1989660Notes

Reaction equation

[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[CH:15]=[C:16]([NH2:20])[CH:17]=[CH:18][CH:19]=3)[N:9]=2)[CH:5]=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[CH:3]=1.C(N(CC)CC)C.[N:38]1([S:44](Cl)(=[O:46])=[O:45])[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1>ClCCl>[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[CH:15]=[C:16]([NH:20][S:44]([N:38]4[CH2:43][CH2:42][O:41][CH2:40][CH2:39]4)(=[O:46])=[O:45])[CH:17]=[CH:18][CH:19]=3)[N:9]=2)[CH:5]=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:28])([F:30])[F:29])=[CH:23][CH:22]=2)[CH:3]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a stirred solution of 3-[6′-methyl-4′-(4-trifluoromethyl-phenyl)-[2,2′]bipyridinyl-6-yl]-phenylamine (example 327) (0.200 g, 0.5 mmol) and triethyl amine (0.21 mL, 1.5 mmol) in dichloromethane (5 mL) was added commercially available morpholine-4-sulfonyl chloride (0.101 mg, 0.55 mmol) and the mixture was stirred at 23° C. for 30 min. Diluted with DCM, washed with sat. NaHCO3-sol. and water, dried the organic layer over Na2SO4. Removal of the solvent in vacuum left a crude product which was purified by silica gel column chromatography with heptane/EtOAc, followed by trituration with heptane/diethyl ether to give the title compound as an off-white solid (0.035 g, 13%). MS (ISP) 555.2 [(M+H)+]; mp 191° C.

Workup

washwashed with sat. NaHCO3-sol
dry with materialand water, dried the organic layer over Na2SO4
customRemoval of the solvent in vacuum
waitleft a crude product which
customwas purified by silica gel column chromatography with heptane/EtOAc

Sources & evidence

ORD record: ord-e5079fc51a374d3b85c35293ee9b4e8e
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642264B2

Reaction notes

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