Pyridine-3-sulfonyl chloride hydrochloride → N-(3-methyl-4-oxo-2-phenyl-3,4-dihydroquinazolin-8-yl)pyridine-3-sulfonamide

HRID 520440

Reaction equation

Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:3]=1.[NH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[N:21]=[C:20]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25](C(F)(F)F)[CH:24]=1)[N:19]([CH3:33])[C:18]2=[O:34]>N1C=CC=CC=1>[CH3:33][N:19]1[C:18](=[O:34])[C:17]2[C:22](=[C:13]([NH:12][S:8]([C:4]3[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=3)(=[O:10])=[O:9])[CH:14]=[CH:15][CH:16]=2)[N:21]=[C:20]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Pyridine-3-sulfonyl chloride hydrochloride 7 (280 mg, 1.3 mmol) was added to a solution of 8-amino-3-methyl-2-(3-(trifluoromethyl)phenyl)quinazolin-4(3H)-one 5 (100 mg, 0.313 mmol) in pyridine (5 mL). The reaction mixture was heated at 80° C. for 12 h. The pyridine was removed in vacuo. The residue was taken up in CH2Cl2, washed with sat. aq NaHCO3, dried (MgSO4) and concentrated. The crude residue was purified by MPLC eluting with CH2Cl2/MeOH (0-10%) followed by recrystallization from CH3CN to give Compound 361 (77 mg, 53% yield). MS (ESI) calcd for C21H15F3N4O3S: 460.08. found: 461 [M+H].

Workup

customThe pyridine was removed in vacuo
washwashed with sat. aq NaHCO3
dry with materialdried (MgSO4)
concentrationconcentrated
customThe crude residue was purified by MPLC
washeluting with CH2Cl2/MeOH (0-10%)
customfollowed by recrystallization from CH3CN

Sources & evidence

ORD record: ord-4b14d276c9464054b64576a01ecda094
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09326986B2

Linked notes

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