Diethyl Ether → [3-(4-Chlorophenyl)-1-[(3-chlorophenyl)-methyl]-4-methyl-5-(trifluoromethyl)-1H-pyrrol-2-yl]-morpholin-4-yl-methanone

HRID 623759노트

반응식

HRID 623759 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH3:13])=[C:11]([C:14]([F:17])([F:16])[F:15])[NH:10][C:9]=2[C:18]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[O:19])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Cl:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=1)[CH2:36]Br.CCOCC>CC#N.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH3:13])=[C:11]([C:14]([F:15])([F:16])[F:17])[N:10]([CH2:36][C:35]3[CH:38]=[CH:39][CH:40]=[C:33]([Cl:32])[CH:34]=3)[C:9]=2[C:18]([N:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)=[O:19])=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 86711843(3-(4-Chlorophenyl)-4-methyl-5-(trifluoromethyl)-1H-pyrrol-2-yl)(morpholino)methanone

생성물 1

HCID 73296604[3-(4-Chlorophenyl)-1-[(3-chlorophenyl)-methyl]-4-methyl-5-(trifluoromethyl)-1H-pyrrol-2-yl]-morpholin-4-yl-methanone

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

(3-(4-Chlorophenyl)-4-methyl-5-(trifluoromethyl)-1H-pyrrol-2-yl)(morpholino)methanone (80 mg, 0.215 mmol) was dissolved in dry MeCN (5 mL). The solution was mixed with K2CO3 (59 mg, 0.429 mmol), followed by addition of 3-chlorobenzyl bromide (31 μL, 0.236 mmol). The reaction mixture was stirred vigorously at 80° C. overnight. The temperature was lowered to room temperature; the reaction mixture was combined with a few lumps of ice, Et2O (50 mL) and H2O (10 mL) to result in a clear two phase system. The phases were separated; the organic phase was washed with brine. Drying (Na2SO4) was followed by concentration in vacuo. The residue was dissolved in MeCN (30 mL), concentrated in vacuo and used for preparative TLC (silica, heptane/EtOAc, 5:1), providing 96 mg (90%) of SC-25 as a fluffy white solid.

후처리

  1. customwas lowered to room temperature
  2. customto result in a clear two phase system
  3. customThe phases were separated
  4. washthe organic phase was washed with brine
  5. dry with materialDrying (Na2SO4)
  6. concentrationwas followed by concentration in vacuo
  7. dissolutionThe residue was dissolved in MeCN (30 mL)
  8. concentrationconcentrated in vacuo
  9. customproviding 96 mg (90%) of SC-25 as a fluffy white solid

출처 및 근거

ORD 기록
ord-f69ae03393fd4465b647259a0e9ae583
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09302988B2

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