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Bicarbonate Ion → (5R,6S,8S)-5-Methyl-6-phenyl-3-[1-(trifluoromethyl)cyclopropyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-amine

HRID 340177
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인쇄 미리보기

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HRID 340177 반응식
[CH3:1][C@H:2]1[N:7]2[C:8]([C:11]3([C:14]([F:17])([F:16])[F:15])[CH2:13][CH2:12]3)=[N:9][N:10]=[C:6]2[C@@H:5]([NH:18]C(=O)OC(C)(C)C)[CH2:4][C@H:3]1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-]>ClCCl>[CH3:1][C@H:2]1[N:7]2[C:8]([C:11]3([C:14]([F:15])([F:16])[F:17])[CH2:13][CH2:12]3)=[N:9][N:10]=[C:6]2[C@@H:5]([NH2:18])[CH2:4][C@H:3]1[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1
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참가 물질

5

반응물 3

HCID 769Bicarbonate IonHCID 6422Trifluoroacetic acidHCID 86698236tert-butyl {(5R,6S,8S)-5-methyl-6-phenyl-3-[1-(trifluoromethyl)cyclopropyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-yl}carbamate

생성물 1

HCID 86698235(5R,6S,8S)-5-Methyl-6-phenyl-3-[1-(trifluoromethyl)cyclopropyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-amine수율 36.4%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

To a solution of crude tert-butyl {(5R,6S,8S)-5-methyl-6-phenyl-3-[1-(trifluoromethyl)cyclopropyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-yl}carbamate (136 mg, 0.31 mmol) in dichloromethane (3.1 mL) was added trifluoroacetic acid (721 μL, 9.4 mmol) and the resulting mixture stirred 30 min. Saturated aqueous bicarbonate was added, and the resulting mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by reverse chromatography (C-18, 95% water/acetonitrile 25% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (38 mg). MS 337.2 (M+1).

후처리

  1. extractionthe resulting mixture was extracted with ethyl acetate (3×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by reverse chromatography (C-18, 95% water/acetonitrile 25% water/acetonitrile with 0.1% trifluoroacetic acid)

출처 및 근거

ORD 기록
ord-45ede06a0c404cf7ae0c7891213208e3
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08895572B2

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