Disodium disulfite → 6-fluoro-8-methyl-2-[4-(4-methyl-piperazin-1-yl)-phenyl]-3H-quinazolin-4-one

HRID 1050963ノート

反応式

HRID 1050963 の反応式
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([F:12])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH3:13][N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=2)[CH2:16][CH2:15]1.S(OS([O-])=O)([O-])=O.[Na+].[Na+]>CN1CCCC1=O>[F:12][C:8]1[CH:7]=[C:3]2[C:2](=[C:10]([CH3:11])[CH:9]=1)[N:1]=[C:24]([C:23]1[CH:22]=[CH:21][C:20]([N:17]3[CH2:16][CH2:15][N:14]([CH3:13])[CH2:19][CH2:18]3)=[CH:27][CH:26]=1)[NH:6][C:4]2=[O:5]

参加物

5

反応物 3

HCID 24346Disodium disulfiteHCID 7365334-(4-Methylpiperazin-1-yl)benzaldehydeHCID 68276549HCID 68276549、化合物

生成物 1

HCID 1362370046-fluoro-8-methyl-2-[4-(4-methyl-piperazin-1-yl)-phenyl]-3H-quinazolin-4-one

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

A solution of 2-amino-5-fluoro-3-methyl-benzamide (84.1 mg, 0.50 mmol), 4-(4-methyl-piperazin-1-yl)-benzaldehyde (123 mg, 0.60 mmol) and sodium disulfite (97 mg, 0.51 mmol) in N-methyl-pyrrolidone (1 ml) is heated to 150° C. and stirred at this temperature for 16 hours. The reaction mixture is allowed to reach room temperature and poured into ice water. The resulting precipitate is collected by filtration, washed with water and dried. The residue is chromatographed on a silica gel column with methanol/dichloromethane as eluent to afford 6-fluoro-8-methyl-2-[4-(4-methyl-piperazin-1-yl)-phenyl]-3H-quinazolin-4-one as brown powder; HPLC/MS 1.47 min (A), [M+H] 353; 1H NMR (400 MHz, DMSO-d6) δ [ppm] 12.34 (s, 1H), 8.69-7.90 (m, 2H), 7.86-7.26 (m, 2H), 7.28-6.73 (m, 2H), 3.33-3.27 (m, 4H), 2.61 (s, 3H), 2.45 (t, J=5.1 Hz, 4H), 2.23 (s, 3H).

後処理

  1. customto reach room temperature
  2. filtrationThe resulting precipitate is collected by filtration
  3. washwashed with water
  4. customdried
  5. customThe residue is chromatographed on a silica gel column with methanol/dichloromethane as eluent

出典と根拠

ORDレコード
ord-abafbaa13b2c43bc8b750ee31bf4775a
出典データセット
uspto-grants-2016_07
特許番号
US09388142B2

反応ノート

読み込み中…