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1-Methyl-3-pyrrolidinol → 2-({[2-(4-Chlorophenyl)-1,3-thiazol-4-yl]methyl}sulphanyl)-6-[(1-methylpyrrolidin-3-yl)oxy]-4-phenylpyridine-3,5-dicarbonitrile

HRID 1630722
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HRID 1630722 반응식
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([CH3:7])[CH2:3]1.Cl[C:9]1[C:14]([C:15]#[N:16])=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([C:23]#[N:24])=[C:11]([S:25][CH2:26][C:27]2[N:28]=[C:29]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)[S:30][CH:31]=2)[N:10]=1>C1COCC1>[Cl:38][C:35]1[CH:36]=[CH:37][C:32]([C:29]2[S:30][CH:31]=[C:27]([CH2:26][S:25][C:11]3[C:12]([C:23]#[N:24])=[C:13]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:14]([C:15]#[N:16])=[C:9]([O:1][CH:2]4[CH2:6][CH2:5][N:4]([CH3:7])[CH2:3]4)[N:10]=3)[N:28]=2)=[CH:33][CH:34]=1
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참가 물질

4

반응물 2

HCID 930741-Methyl-3-pyrrolidinolHCID 866542112-Chloro-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulphanyl)-4-phenylpyridine-3,5-dicarbonitrile

생성물 1

HCID 445487102-({[2-(4-Chlorophenyl)-1,3-thiazol-4-yl]methyl}sulphanyl)-6-[(1-methylpyrrolidin-3-yl)oxy]-4-phenylpyridine-3,5-dicarbonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

25 μl (0.229 mmol) of 3-hydroxy-N-methylpyrrolidine are initially charged in 0.5 ml of THF, the mixture is cooled to 0° C., 249 μl (0.249 mmol) of phosphazene base P(4)-t-Bu (1M in THF) are added and the mixture is stirred at this temperature for 10 minutes. 120 mg (0.208 mmol) of the compound from Example 3A are then added, and the mixture is stirred at RT overnight. The reaction mixture is then purified by preparative HPLC (addition of 0.15% hydrochloric acid). This gives 38 mg of the impure target compound. This is dissolved in dichloromethane and washed twice with 1N hydrochloric acid, once with water and once with saturated aqueous sodium chloride solution. After drying over sodium sulphate, the organic phase is concentrated on a rotary evaporator and the crude product is purified once more by preparative HPLC (addition of 0.15% hydrochloric acid).

후처리

  1. stirringthe mixture is stirred at RT overnight
  2. customThe reaction mixture is then purified by preparative HPLC (addition of 0.15% hydrochloric acid)
  3. dissolutionThis is dissolved in dichloromethane
  4. washwashed twice with 1N hydrochloric acid, once with water and once with saturated aqueous sodium chloride solution
  5. dry with materialAfter drying over sodium sulphate
  6. concentrationthe organic phase is concentrated on a rotary evaporator
  7. customthe crude product is purified once more by preparative HPLC (addition of 0.15% hydrochloric acid)

출처 및 근거

ORD 기록
ord-0bad6556df0b4ccb8e1fc7d6b4d0ece0
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08791146B2

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