2-Bromo-N,N-dimethylacetamide → 7-N-(tert-Butoxycarbonyl)-8-[2-(dimethylamino)-2-oxoethyl]-2-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-alpha]pyrazine

HRID 133080노트

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HRID 133080 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[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N-]C(C)C)(C)C.[Li+].Br[CH2:30][C:31]([N:33]([CH3:35])[CH3:34])=[O:32]>O1CCCC1.CCCCCCC.O1CCCC1.C(C1C=CC=CC=1)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[N:14]=[C:15]([C:17]([F:18])([F:19])[F:20])[N:16]=[C:10]2[CH:9]1[CH2:30][C:31]([N:33]([CH3:35])[CH3:34])=[O:32])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 3

HCID 2255442-Bromo-N,N-dimethylacetamideHCID 2724682Lithium diisopropylamideHCID 53393358tert-Butyl 2-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[1,5-a]pyrazine-7(8H)-carboxylate

생성물 1

HCID 693632797-N-(tert-Butoxycarbonyl)-8-[2-(dimethylamino)-2-oxoethyl]-2-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-alpha]pyrazine

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 22742125Tetrahydrofuran heptane ethylbenzol용매

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온도
-78 °C

실험 절차

To a solution of 2.13 g (7.30 mmol) of 7-N-(tert-butoxycarbonyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-α]pyrazine (Example 2, Step A) in 10 mL of tetrahydrofuran at −78° C. was added lithium diisopropylamide (4.02 mL of a 2.0M solution in heptane/tetrahydrofuran/ethylbenzene, 8.03 mmol). The mixture was allowed to stir at −78° C. for 15 min, and then 2-bromo-N,N-dimethylacetamide from Step A in 5 mL of tetrahydrofuran was added, and the mixture slowly warmed to ambient temperature over 18 h. The reaction was quenched with aqueous ammonium chloride and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated. Purification by flash chromatography (silica gel, gradient of 50% to 75% ethyl acetate/hexane) yielded the title compound. LC/MS 322 ((M+1)-t-butyl).

후처리

  1. temperaturethe mixture slowly warmed to ambient temperature over 18 h
  2. customThe reaction was quenched with aqueous ammonium chloride
  3. extractionthe aqueous layer was extracted three times with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customPurification by flash chromatography (silica gel, gradient of 50% to 75% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-afcf7d6503a34e199fae461b24d58255
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390809B2

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