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Citric Acid → 4-[(4-methylpiperazin-1-yl)methyl]-N-{5-methyl-4-[(4-(pyrid-3-yl)pyrimid-2-yl)amino]pyrid-2-yl}-3-(trifluoromethyl)benzamide

HRID 1926596
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HRID 1926596 반응식
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([NH:9][C:10](=[O:29])[C:11]2[CH:16]=[CH:15][C:14]([CH2:17][N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)=[C:13]([C:25]([F:28])([F:27])[F:26])[CH:12]=2)[CH:3]=1.S([C:34]1[N:39]=[C:38]([C:40]2[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=2)[CH:37]=[CH:36][N:35]=1)(C)(=O)=O.[H-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)(Cl)Cl.CO.CN(C=O)C>[CH3:24][N:21]1[CH2:20][CH2:19][N:18]([CH2:17][C:14]2[CH:15]=[CH:16][C:11]([C:10]([NH:9][C:4]3[CH:3]=[C:2]([NH:1][C:34]4[N:39]=[C:38]([C:40]5[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=5)[CH:37]=[CH:36][N:35]=4)[C:7]([CH3:8])=[CH:6][N:5]=3)=[O:29])=[CH:12][C:13]=2[C:25]([F:28])([F:27])[F:26])[CH2:23][CH2:22]1
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참가 물질

7

반응물 4

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 469098552-(Methylsulfonyl)-4-(pyridin-3-yl)pyrimidineHCID 69229345N-(4-amino-5-methylpyridin-2-yl)-4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)benzamide

생성물 1

HCID 692318604-[(4-methylpiperazin-1-yl)methyl]-N-{5-methyl-4-[(4-(pyrid-3-yl)pyrimid-2-yl)amino]pyrid-2-yl}-3-(trifluoromethyl)benzamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 21584188Chloroform methanol용매

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온도
0 °C

실험 절차

To a flask was added N-(4-amino-5-methylpyridin-2-yl)-4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)benzamide (7.1 g), 2-mesyl-4-(3-pyridyl)pyrimidine (5.0 g) and DMF (50 mL). After the solution was cooled to about 0° C., sodium hydride (60%, 1.5 g) was added in several portions and the reaction was stirred at the same temperature for 2 hours, then warmed up to room temperature for 1 hour. A mixture solvent of chloroform/methanol (30:1, 100 mL) was added and the PH value was adjusted to 7 using 10% citric acid. The aqueous phase was extracted, then the organic combined phase was washed with brine, dried, filtered, concentrated and Purified through column chromatography to give the title compound.

후처리

  1. temperaturewarmed up to room temperature for 1 hour
  2. extractionThe aqueous phase was extracted
  3. washthe organic combined phase was washed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurified through column chromatography

출처 및 근거

ORD 기록
ord-58a96b113ae14d62a77ed7eac51ac972
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08183242B2

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