Thionyl Chloride → 4-(4-chloro-5-trifluoromethyl-pyrimidin-2-ylamino)-3-methoxy-N-(1-methyl-piperidin-4-yl)-benzamide

HRID 1626357ノート

反応式

HRID 1626357 の反応式
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][C:14]=2[O:22][CH3:23])[N:3]=1.S(Cl)(Cl)=O.[NH2:28][CH:29]1[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]1.C(N(C(C)C)CC)(C)C>C1(C)C=CC=CC=1.C1COCC1>[Cl:1][C:2]1[C:7]([C:8]([F:10])([F:9])[F:11])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH:28][CH:29]3[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]3)=[O:19])=[CH:15][C:14]=2[O:22][CH3:23])[N:3]=1

参加物

7

反応物 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 27375314-Amino-1-methylpiperidineHCID 589063992-(4-Carboxy-2-methoxy-phenylamino)-4-chloro-5-trifluoromethyl-pyrimidine

生成物 1

HCID 582009164-(4-chloro-5-trifluoromethyl-pyrimidin-2-ylamino)-3-methoxy-N-(1-methyl-piperidin-4-yl)-benzamide

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
110 °C

実験手順

4-(4-chloro-5-trifluoromethyl-pyrimidin-2-ylamino)-3-methoxy-benzoic acid (5 g) is suspended in toluene (150 mL) and combined with thionyl chloride (1.77 mL), stirred for 2 h at 110° C. and after cooling the solvent is eliminated in vacuo. The residue is taken up in THF (50 mL), cooled to 0° C. and a solution of 4-amino-1-methylpiperidine (1.396 g) and diisopropylethylamine (4.19 mL) is added dropwise thereto. Then the reaction mixture is left to warm up to RT and stirred overnight. After filtering, the residue is dried overnight at 50° C.

後処理

  1. temperatureafter cooling the solvent
  2. temperaturecooled to 0° C.
  3. waitThen the reaction mixture is left
  4. temperatureto warm up to RT
  5. stirringstirred overnight
  6. filtrationAfter filtering
  7. customthe residue is dried overnight at 50° C.

出典と根拠

ORDレコード
ord-2225b8238be5420d9a64f2a7dccfb7a4
出典データセット
uspto-grants-2014_07
特許番号
US08785464B2

反応ノート

読み込み中…