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 1019620노트

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HRID 1019620 반응식
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]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 5213051-Chloroethyl chloroformateHCID 66934181HCID 66934181, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 6344Dichloromethane용매HCID 63651,1-Dichloroethane용매

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온도
22 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9f24bab77b0c4a8dacad2da46856a917
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716276B2

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