1,1'-Thiocarbonyldiimidazole → tert-Butyl 8-(cyclopropylmethylene)-2-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[1,5-alpha]pyrazine-7(8H)-carboxylate

HRID 133070노트

반응식

HRID 133070 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[N:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[N:16]=[C:10]2[CH:9]1[CH:21]([CH:23]1[CH2:25][CH2:24]1)O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1N=CN(C(N2C=NC=C2)=S)C=1>CN(C)C1C=CN=CC=1.ClC(Cl)C>[CH:23]1([CH:21]=[C:9]2[N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12][N:11]3[N:14]=[C:15]([C:17]([F:18])([F:19])[F:20])[N:16]=[C:10]23)[CH2:25][CH2:24]1

참가 물질

5

반응물 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 69364591[7-N-(tert-Butoxycarbonyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-alpha]pyrazin-8-yl](cyclopropyl)methanol

생성물 1

HCID 69362860tert-Butyl 8-(cyclopropylmethylene)-2-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[1,5-alpha]pyrazine-7(8H)-carboxylate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 63651,1-Dichloroethane용매

실험 절차

A solution of 100 mg (0.28 mmol) of [7-N-(tert-butoxycarbonyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydro [1,2,4]triazolo[1,5-α]pyrazin-8-yl](cyclopropyl)methanol (prepared as outlined in Example 3, Step A), 52.4 mg (0.294 mmol) of 1,1-thiocarbonyldiimidazole, and 3.4 mg (0.028 mmol) of 4-(dimethylamino)pyridine in 2.0 mL of dichloroethane was stirred at reflux temperature for 17 h. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate. The aqueous phase was extracted with three portions of ethyl acetate. The combined organics were washed with brine, dried over magnesium sulfate and concentrated. Purification by preparative TLC (silica gel) gave the title compound as a clear semi-solid.

후처리

  1. temperatureat reflux temperature for 17 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate
  4. extractionThe aqueous phase was extracted with three portions of ethyl acetate
  5. washThe combined organics were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customPurification by preparative TLC (silica gel)

출처 및 근거

ORD 기록
ord-ffb46fd82e0a4023b0a402c3da64673f
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390809B2

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