1-Chloroethyl chloroformate → HCID 67468519、化合物

HRID 1429535ノート

反応式

HRID 1429535 の反応式
C([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[S:16][C:17]3[CH:23]=[C:22]([C:24]4[CH2:25][CH2:26][N:27]([S:30]([CH2:33][CH2:34][CH3:35])(=[O:32])=[O:31])[CH2:28][CH:29]=4)[CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C(Cl)(=O)OC(Cl)C>ClC(Cl)C.C(Cl)Cl>[NH:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[S:16][C:17]3[CH:23]=[C:22]([C:24]4[CH2:25][CH2:26][N:27]([S:30]([CH2:33][CH2:34][CH3:35])(=[O:32])=[O:31])[CH2:28][CH:29]=4)[CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:12][CH2:13]1

参加物

5

反応物 2

HCID 5213051-Chloroethyl chloroformateHCID 545964042-(I-benzylpiperidin-4-yloxy)-6-(1-(propylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazole

生成物 1

HCID 67468519HCID 67468519、化合物収率 94.1%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 63651,1-Dichloroethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 2-(I-benzylpiperidin-4-yloxy)-6-(1-(propylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazole (1.812 g, 3.54 mmol) in dichloroethane (30 mL) at 0° C. was added 1-chloroethyl carbonochloridate (0.497 mL, 4.60 mmol). Upon completion of addition, the reaction mixture was stirred at 0° C. for 15 min and then heated to reflux, where it stirred for 1 h. At the conclusion of this period, the volatiles were removed under vacuum and the resulting sample was dissolved in MeOH (30 mL) and then heated to reflux, where it stirred for 1 h. After this time, the reaction mixture was cooled to rt and then concentrated under reduced pressure to yield a residue. The residue was diluted with CH2Cl2 and washed with aq K2CO3 (saturated, 10 mL) and brine (10 mL). The organic layer was dried (Na2SO4), filtered, and then concentrated to afford Compound 15A (1.405 g, 3.33 mmol, 94% yield). LC/MS (m/z)=422 (M+H)+.

後処理

  1. additionUpon completion of addition
  2. temperatureheated
  3. temperatureto reflux
  4. stirringwhere it stirred for 1 h
  5. customAt the conclusion of this period, the volatiles were removed under vacuum
  6. dissolutionthe resulting sample was dissolved in MeOH (30 mL)
  7. temperatureheated
  8. temperatureto reflux
  9. stirringwhere it stirred for 1 h
  10. temperatureAfter this time, the reaction mixture was cooled to rt
  11. concentrationconcentrated under reduced pressure
  12. customto yield a residue
  13. washwashed with aq K2CO3 (saturated, 10 mL) and brine (10 mL)
  14. dry with materialThe organic layer was dried (Na2SO4)
  15. filtrationfiltered
  16. concentrationconcentrated

出典と根拠

ORDレコード
ord-22fa99c149c54e6287a268305bc248dd
出典データセット
uspto-grants-2015_01
特許番号
US08940716B2

反応ノート

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