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

HRID 520440

反応式

HRID 520440 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
80 °C

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-4b14d276c9464054b64576a01ecda094
出典データセット
uspto-grants-2016_05
特許番号
US09326986B2

関連ノート

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