Water → HCID 178441138, 화합물

HRID 253706노트

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HRID 253706 반응식
Cl[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])[N:3]=1.[NH:22]1[C:26]2=[N:27][CH:28]=[CH:29][CH:30]=[C:25]2[C:24]([NH2:31])=[N:23]1.O.C(=O)(O)[O-].[Na+]>CN1CCCC1=O>[C:8]([C:6]1[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])[N:3]=[C:2]([NH:31][C:24]2[C:25]3[C:26](=[N:27][CH:28]=[CH:29][CH:30]=3)[NH:22][N:23]=2)[CH:7]=1)([CH3:11])([CH3:10])[CH3:9]

참가 물질

6

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HCID 962WaterHCID 516892Sodium BicarbonateHCID 179793884-Chloro-6-tert-butyl-2-(2-trifluoromethylphenyl)-pyrimidineHCID 178509226HCID 178509226, 화합물

생성물 1

HCID 178441138HCID 178441138, 화합물수율 5.3%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
165 °C

실험 절차

A mixture of 4-chloro-6-tert-butyl-2-(2-trifluoromethyl-phenyl)-pyrimidine (0.10 g, 0.32 mmol) and 1H-pyrazolo[3,4-b]pyridin-3-ylamine (0.064 g, 0.48 mmol) was heated neat at 160-170° C. for 16 hours. The resulting residue was cooled, dissolved in N-methyl-pyrrolidinone (2 mL), then poured into water (20 mL) and sodium bicarbonate (5 mL) and extracted twice with ethyl acetate. The combined organic layers were washed four times with water, once with brine, then dried over sodium sulfate and concentrated. The crude product was purified by preparative HPLC to provide the title compound (0.007 g, 4% yield) as a yellow solid. 1H-NMR (500 MHz, DMSO-d6) δ 13.2 (br s, 1H), 10.6 (br s, 1H), 8.49 (m, 2H), 7.84 (d, J=7.8 Hz, 2H), 7.76 (m, 2H), 7.68 (m, 1H), 7.12 (m, 1H), 1.32 (s, 9H) ppm; LC-MS 413.08 (M+H); Rt (Method A) 3.112 minutes.

후처리

  1. temperatureThe resulting residue was cooled
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layers were washed four times with water
  4. dry with materialonce with brine, then dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-2d0dece3dd644c4b954241da15b1fbe6
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872129B2

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