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 429623노트

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HRID 429623 반응식
[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]

참가 물질

5

반응물 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-one2회

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6fb7eb27a99c4656a096906a7811d700
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06316482B1

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