Trifluoroacetic acid → [8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(3-piperazin-1-yl-phenyl)-amine

HRID 472468

반응식

HRID 472468 반응식
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]3[N:39]=[C:24]4[C:25]([C:29]5[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:31][CH:30]=5)=[CH:26][CH:27]=[CH:28][N:23]4[N:22]=3)[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:38][S:35]([C:32]1[CH:33]=[CH:34][C:29]([C:25]2[C:24]3[N:23]([N:22]=[C:21]([NH:20][C:16]4[CH:17]=[CH:18][CH:19]=[C:14]([N:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]5)[CH:15]=4)[N:39]=3)[CH:28]=[CH:27][CH:26]=2)=[CH:30][CH:31]=1)(=[O:36])=[O:37]

참가 물질

5

반응물 2

HCID 6422Trifluoroacetic acidHCID 596124154-{3-[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 59612339[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(3-piperazin-1-yl-phenyl)-amine

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 10340Sodium Carbonate용매

실험 절차

To a solution of 4-{3-[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester (250.0 mg, 0.4556 mmol) in dichloromethane (1 mL) was added dropwise trifluoroacetic acid (0.40 mL, 5.2 mmol) and the mixture was stirred at room temperature for 6 hours. The mixture was diluted with dichloromethane (20 mL) and saturated aqueous sodium carbonate (10 mL) was added dropwise. The mixture was stirred for 30 minutes. The layers were separated and the aqueous was washed with dichloromethane (3×10 mL). The combined organic layers were dried over magnesium sulfate, filtered and evaporated under reduced pressure. [8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(3-piperazin-1-yl-phenyl)-amine was isolated as a yellow foam (0.168 g, 82%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.49 (d, J=6.7 Hz, 1H), 8.25 (d, J=8.4 Hz, 2H), 8.08 (d, J=8.4 Hz, 2H), 7.65 (d, J=7.2 Hz, 1H), 7.36 (s, 1H), 7.23 (t, J=8.3 Hz, 1H), 7.04-6.96 (m, 2H), 6.86 (s, 1H), 6.60 (d, J=8.3 Hz, 1H), 3.24-3.19 (m, 4H), 3.10 (s, 3H), 3.09-3.04 (m, 4H). MS=449 (MH)+.

후처리

  1. additionwas added dropwise
  2. stirringThe mixture was stirred for 30 minutes
  3. customThe layers were separated
  4. washthe aqueous was washed with dichloromethane (3×10 mL)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-1e34891f5db64c9ca3453158b01397c2
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633173B2

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