Sodium Hydroxide → 3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]-4-(3-nitro-2-trifluoroacetylaminobenzoyl)aminobenzamide

HRID 429623ノート

反応式

HRID 429623 の反応式
[NH2:1][C:2]1[CH:33]=[CH:32][C:5]([C:6]([N:8]([CH3:31])[C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=2[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[O:23])=[O:7])=[CH:4][C:3]=1[O:34][CH3:35].[N+:36]([C:39]1[C:48]2[N:47]=[C:46]([C:49]([F:52])([F:51])[F:50])[O:45][C:44](=[O:53])[C:43]=2[CH:42]=[CH:41][CH:40]=1)([O-:38])=[O:37].[OH-].[Na+]>O1CCOCC1>[CH3:35][O:34][C:3]1[CH:4]=[C:5]([CH:32]=[CH:33][C:2]=1[NH:1][C:44](=[O:53])[C:43]1[CH:42]=[CH:41][CH:40]=[C:39]([N+:36]([O-:38])=[O:37])[C:48]=1[NH:47][C:46](=[O:45])[C:49]([F:51])([F:52])[F:50])[C:6]([N:8]([CH3:31])[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]1)=[O:23])=[O:7]

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 183549064-amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamideHCID 183549908-Nitro-2-trifluoromethyl-3,1-benzoxazin-4-one2 回

生成物 1

HCID 183552993-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]-4-(3-nitro-2-trifluoroacetylaminobenzoyl)aminobenzamide収率 114.8%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a solution of 4-amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (6.0 g) in 1,4-dioxane (200 ml) was added 8-nitro-2-trifluoromethyl-3,1-benzoxazin-4-one (3.24 g) and the mixture was stirred at 100° C. for 4 hours. To the mixture was added 8-nitro-2-trifluoromethyl-3,1-benzoxazin-4-one (3.24 g). and the solution was stirred at 100° C. for additional 3 hours. To the mixture was added 1N sodium hydroxide solution (90 ml) and the resulting solution was stirred at 60° C. for 1 hour. After being concentrated in vacuo, the residue was diluted with chloroform and the organic solution was washed with saturated aqueous sodium bicarbonate solution and brine. The organic layer was dried over magnesium sulfate and the solvent was concentrated in vacuo to give 3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]-4-(3-nitro-2-trifluoroacetylaminobenzoyl)aminobenzamide as a yellow powder (10.6 g). The crude product was used for next step without further purification.

後処理

  1. stirringand the solution was stirred at 100° C. for additional 3 hours
  2. stirringthe resulting solution was stirred at 60° C. for 1 hour
  3. concentrationAfter being concentrated in vacuo
  4. additionthe residue was diluted with chloroform
  5. washthe organic solution was washed with saturated aqueous sodium bicarbonate solution and brine
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationthe solvent was concentrated in vacuo

出典と根拠

ORDレコード
ord-6fb7eb27a99c4656a096906a7811d700
出典データセット
uspto-grants-2001_11
特許番号
US06316482B1

反応ノート

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