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

HRID 520440

반응식

HRID 520440 반응식
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

참가 물질

4

반응물 2

HCID 12571517Pyridine-3-sulfonyl chloride hydrochlorideHCID 585528228-amino-3-methyl-2-(3-(trifluoromethyl)phenyl)quinazolin-4(3H)-one

생성물 1

HCID 67993194N-(3-methyl-4-oxo-2-phenyl-3,4-dihydroquinazolin-8-yl)pyridine-3-sulfonamide수율 62.7%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
80 °C

실험 절차

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].

후처리

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

출처 및 근거

ORD 기록
ord-4b14d276c9464054b64576a01ecda094
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09326986B2

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