Potassium Carbonate → 1-(3-Chloro-5,6,7,8-tetrahydro-4H-thieno[2,3-d]azepin-2-yl)-2,2-dimethyl-propan-1-one

HRID 1019620ノート

反応式

HRID 1019620 の反応式
C([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([Cl:24])=[C:16]([C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[S:17][C:11]=2[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].ClC(OC(Cl)C)=O>ClC(Cl)C.C(Cl)Cl.CO>[Cl:24][C:15]1[C:12]2[CH2:13][CH2:14][NH:8][CH2:9][CH2:10][C:11]=2[S:17][C:16]=1[C:18](=[O:23])[C:19]([CH3:21])([CH3:20])[CH3:22]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 5213051-Chloroethyl chloroformateHCID 66934181HCID 66934181、化合物

生成物 1

HCID 247833691-(3-Chloro-5,6,7,8-tetrahydro-4H-thieno[2,3-d]azepin-2-yl)-2,2-dimethyl-propan-1-one

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒HCID 63651,1-Dichloroethane溶媒

反応条件

温度
22 °C

実験手順

A solution of the product from step (h) (assumed 0.35 mmol) in anhydrous dichloroethane (2 ml) was cooled to 0° C., treated with K2CO3 (−50 mg) and 1-chloroethyl chloroformate (0.38 ml, 3.5 mmol). The reaction was allowed to warmed to 22° C. for 18 hours. The reaction diluted with CH2Cl2 (50 ml) and washed with sat. NaHCO3 (2×50 ml), brine (50 ml), dried (MgSO4) and solvent evaporated in vacuo providing an oily residue, which was dissolved in anhydrous MeOH (10 ml) and refluxed for 1.5 hours. The MeOH was evaporated in vacuo to give the crude product. A portion of the crude was purified by preparative HPLC-MS to give the title compound. 1H NMR (300 MHz, CDCl3) δ 6.25 (br s, 1H); 3.05-3.19 (m, 8H); 1.34 (s, 9H); MS: ESI (positive): 272, 274 (M+H).

後処理

  1. washwashed with sat. NaHCO3 (2×50 ml), brine (50 ml)
  2. dry with materialdried (MgSO4) and solvent
  3. customevaporated in vacuo
  4. customproviding an oily residue, which
  5. temperaturerefluxed for 1.5 hours
  6. customThe MeOH was evaporated in vacuo
  7. customto give the crude product
  8. customA portion of the crude was purified by preparative HPLC-MS

出典と根拠

ORDレコード
ord-9f24bab77b0c4a8dacad2da46856a917
出典データセット
uspto-grants-2014_05
特許番号
US08716276B2

反応ノート

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