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

HRID 1626357노트

반응식

HRID 1626357 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
110 °C

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-2225b8238be5420d9a64f2a7dccfb7a4
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785464B2

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