Water → (5-Fluoro-1H-indazol-3-yl)-[6-methyl-2-(2-trifluoromethyl-phenyl)-pyrimidin-4-yl]amine

HRID 253703

반응식

HRID 253703 반응식
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([F:18])([F:17])[F:16])[N:3]=1.[F:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][N:24]=[C:23]2[NH2:29].O.C(=O)(O)[O-].[Na+]>CN1CCCC1=O>[F:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][N:24]=[C:23]2[NH:29][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([F:18])([F:17])[F:16])[N:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 43278965-fluoro-1H-indazol-3-amineHCID 219392714-Chloro-6-methyl-2-(2-trifluoromethyl-phenyl)-pyrimidine

생성물 1

HCID 10385522(5-Fluoro-1H-indazol-3-yl)-[6-methyl-2-(2-trifluoromethyl-phenyl)-pyrimidin-4-yl]amine수율 56.5%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
165 °C

실험 절차

A mixture of 4-chloro-6-methyl-2-(2-trifluoromethyl-phenyl)-pyrimidine (0.10 g, 0.37 mmol) and 5-fluoro-1H-indazole-3-ylamine (0.072 g, 0.48 mmol) was heated neat at 160-170° C. for 8 hours. The resulting residue was cooled to ambient temperature then dissolved in N-methyl-pyrrolidinone (2 mL). This mixture was poured into water (20 mL) and sodium bicarbonate (5 mL) was added and the resulting mixture filtered, washing with water. Purification by preparative HPLC provided the title compound (0.081 g, 43% yield) as a tan solid. 1H-NMR (500 MHz, DMSO-d6) δ 12.8 (br s, 1H), 10.6 (br s, 1H), 7.86 (d, J=8.0 Hz, 1H), 7.77 (m, 4H), 7.62 (br s, 1H), 7.50 (m, 1H), 7.29 (m, 1H), 2.44 (s, 3H) ppm; LC-MS 388.05 (M+H); Rt (Method A) 2.900 minutes.

후처리

  1. temperatureThe resulting residue was cooled to ambient temperature
  2. additionwas added
  3. filtrationthe resulting mixture filtered
  4. washwashing with water
  5. customPurification by preparative HPLC

출처 및 근거

ORD 기록
ord-9502545c17784914b5a2cfe4a1d4e8bc
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872129B2

연결된 노트

불러오는 중…