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

HRID 1725589

反応式

HRID 1725589 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
165 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c3208dd52f5a409da9fa3114d393fd99
出典データセット
uspto-grants-2009_02
特許番号
US07491730B2

関連ノート

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