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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Triethylamine → N-(2-{[(3R)-1-(5-Hydroxy-5-pyridin-3-ylbicyclo[2.2.2]oct-2-yl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide

HRID 1016083
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HRID 1016083 반응식
Cl.[O:2]=[C:3]([NH:18][C@@H:19]1[CH2:23][CH2:22][NH:21][CH2:20]1)[CH2:4][NH:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1.[OH:24][C:25]1([C:34]2[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=2)[CH2:30][CH:29]2[CH2:31][CH2:32][CH:26]1[CH2:27][C:28]2=O.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[OH:24][C:25]1([C:34]2[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=2)[CH2:30][CH:29]2[CH2:31][CH2:32][CH:26]1[CH2:27][CH:28]2[N:21]1[CH2:22][CH2:23][C@@H:19]([NH:18][C:3](=[O:2])[CH2:4][NH:5][C:6](=[O:17])[C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:15])([F:16])[F:14])[CH:8]=2)[CH2:20]1
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참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 595560585-Hydroxy-5-pyridin-3-ylbicyclo[2.2.2]octan-2-oneHCID 66787629N-{2-Oxo-2-[(3R)-pyrrolidin-3-ylamino]ethyl}-3-(trifluoromethyl)benzamide hydrochloride

생성물 1

HCID 59556078N-(2-{[(3R)-1-(5-Hydroxy-5-pyridin-3-ylbicyclo[2.2.2]oct-2-yl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

N-{2-Oxo-2-[(3R)-pyrrolidin-3-ylamino]ethyl}-3-(trifluoromethyl)benzamide hydrochloride (100 mg, 0.284 mmol) and 5-hydroxy-5-pyridin-3-ylbicyclo[2.2.2]octan-2-one (62.0 mg, 0.284 mmol) were dissolved in dry THF (10 mL). Triethylamine (80 uL, 0.57 mmol) and sodium triacetoxyborohydride (120 mg, 0.57 mmol) were added and the mixture was stirred at room temperature overnight. TLC indicated conversion to desired products in about a 1:1 ratio of isomers. Adsorbed reaction mixture onto silica gel and chromatographed eluting with dichloromethane to 10% methanol/dichloromethane/0.5% ammonium hydroxide. Fractions were combined to give pure higher Rf isomer and pure lower Rf isomer: Higher Rf product: LC/MS (positive ion) m/z=517.1 (M+H)+; Lower Rf product: LC/MS (positive ion) m/z=517.2 (M+H)+.

후처리

  1. customAdsorbed reaction mixture onto silica gel
  2. customchromatographed
  3. washeluting with dichloromethane to 10% methanol/dichloromethane/0.5% ammonium hydroxide
  4. customto give pure higher Rf isomer and pure lower Rf isomer

출처 및 근거

ORD 기록
ord-15ff3d8e2d2f44b7ae2e2c559099b2b1
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07985730B2

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