Trifluoroacetic acid → 1-{2-[6-(4,4-Difluoropiperidin-1-yl)pyrimidin-4-yl]-3-oxo-2,3-dihydro-1H-pyrazol-4-yl}-1H-1,2,3-triazole-4-carbonitrile

HRID 2039495ノート

反応式

HRID 2039495 の反応式
Cl[C:2]1[CH:7]=[C:6]([NH:8][NH2:9])[N:5]=[CH:4][N:3]=1.Cl.[F:11][C:12]1([F:18])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(N(C(C)C)C(C)C)C.FC(F)(F)C(O)=O.CN(C)[CH:37]=[C:38]([N:44]1[CH:48]=[C:47]([C:49]#[N:50])[N:46]=[N:45]1)[C:39](OCC)=[O:40]>O>[F:11][C:12]1([F:18])[CH2:17][CH2:16][N:15]([C:2]2[N:3]=[CH:4][N:5]=[C:6]([N:8]3[C:39](=[O:40])[C:38]([N:44]4[CH:48]=[C:47]([C:49]#[N:50])[N:46]=[N:45]4)=[CH:37][NH:9]3)[CH:7]=2)[CH2:14][CH2:13]1

参加物

7

反応物 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 2472224-Chloro-6-hydrazinylpyrimidineHCID 27583514,4-Difluoropiperidine hydrochlorideHCID 66725972Ethyl 2-(4-cyanotriazol-1-yl)-3-(dimethylamino)prop-2-enoate

生成物 1

HCID 444648671-{2-[6-(4,4-Difluoropiperidin-1-yl)pyrimidin-4-yl]-3-oxo-2,3-dihydro-1H-pyrazol-4-yl}-1H-1,2,3-triazole-4-carbonitrile

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A mixture of 200 mg (1.4 mmol) of the compound from Example 11A, 262 mg (1.7 mmol) of 4,4-difluoropiperidine hydrochloride and 289 μl (215 mg, 1.7 mmol) of N-ethyl-N-(propan-2-yl)propane-2-amine in 3 ml of water is stirred at 100° C. for 16 h. Following the addition of 53 μl (79 mg, 0.7 mmol) of trifluoroacetic acid and 325 mg (1.4 mmol) of the compound from Example 7A, the reaction mixture is stirred at 100° C. for 16 h. The precipitated solid is filtered off and washed first with water and then with diethyl ether. The product is dried under reduced pressure. Yield: 34 mg (7% of theory)

後処理

  1. stirringthe reaction mixture is stirred at 100° C. for 16 h
  2. filtrationThe precipitated solid is filtered off
  3. washwashed first with water
  4. customThe product is dried under reduced pressure

出典と根拠

ORDレコード
ord-b65d5c53e9fc4732827d380c6a3a06bb
出典データセット
uspto-grants-2013_11
特許番号
US08580778B2

反応ノート

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