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Water → [6-Cyclopropyl-2-(2-trifluoromethyl-phenyl)-pyrimidin-4-yl]-(1H-indazol-3-yl)-amine

HRID 253709
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HRID 253709 반응식
Cl[C:2]1[CH:7]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[N:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([F:20])([F:19])[F:18])[N:3]=1.[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([NH2:30])=[N:22]1.O.C(=O)(O)[O-].[Na+]>CN1CCCC1=O>[CH:8]1([C:6]2[N:5]=[C:4]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:17]([F:20])([F:19])[F:18])[N:3]=[C:2]([NH:30][C:23]3[C:24]4[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=4)[NH:21][N:22]=3)[CH:7]=2)[CH2:10][CH2:9]1
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6

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HCID 962WaterHCID 133991H-indazol-3-amineHCID 516892Sodium BicarbonateHCID 179793904-Chloro-6-cyclopropyl-2-(2-trifluoromethyl-phenyl)pyrimidine

생성물 1

HCID 10475775[6-Cyclopropyl-2-(2-trifluoromethyl-phenyl)-pyrimidin-4-yl]-(1H-indazol-3-yl)-amine수율 15.9%

시약·촉매·용매 1

HCID 13387
N-methyl-2-pyrrolidone
용매

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온도
165 °C

실험 절차

A mixture of 4-chloro-6-cyclopropyl-2-(2-trifluoromethyl-phenyl)-pyrimidine (0.08 g, 0.27 mmol) and 1H-indazol-3-ylamine (0.036 g, 0.41 mmol) was heated neat at 160-170° C. for 6 hours. The residue was cooled and dissolved in N-methyl-pyrrolidinone (2 mL), poured into water (30 mL) and sodium bicarbonate (5 mL) then filtered, washing with water and ether. The collected precipitate and the ether wash were combined and concentrated. Purification by flash chromatography [SiO2, methanol:dichloromethane (2:98)] provided the title compound (0.017 g, 15% yield) as a pale yellow solid. 1H-NMR (500 MHz, DMSO-d6) δ 12.6 (br s, 1H), 10.2 (br s, 1H), 8.00 (d, J=8.1 Hz, 2H), 7.81 (d, J=7.9 Hz, 1H), 7.71 (m, 3H), 7.65 (t, J=7.3 Hz, 1H), 7.45 (d, J=8.4 Hz, 1H), 7.36 (t, J=7.5 Hz, 1H), 7.06 (t, J=7.5 Hz, 1H), 2.04 (m, 1H), 1.01 (m, 2H), 0.96 (m, 2H) ppm; LC-MS 396.10 (M+H); Rt (Method A) 3.122 minutes.

후처리

  1. temperatureThe residue was cooled
  2. filtrationthen filtered
  3. washwashing with water and ether
  4. washThe collected precipitate and the ether wash
  5. concentrationconcentrated
  6. customPurification by flash chromatography [SiO2, methanol:dichloromethane (2:98)]

출처 및 근거

ORD 기록
ord-166647de28204511910a1764938eefa4
출처 데이터셋
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07872129B2

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