1-Hydroxybenzotriazole → 4-(5-bromo-2-chloropyrimidin-4-yl)-N-((S)-2,3-dihydro-1H-inden-1-yl)morpholine-3-carboxamide

HRID 1631735노트

반응식

HRID 1631735 반응식
[Br:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH:10]2[C:15]([OH:17])=O)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.ON1C2C=CC=CC=2N=N1.[C@@H:28]1([NH2:37])[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29]1.Cl.C(N=C=NCCCN(C)C)C>O1CCOCC1>[Br:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH:10]2[C:15]([NH:37][C@@H:28]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:30][CH2:29]2)=[O:17])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

참가 물질

6

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 70000841-Aminoindane, (S)-HCID 86670107HCID 86670107, 화합물

생성물 1

HCID 866701214-(5-bromo-2-chloropyrimidin-4-yl)-N-((S)-2,3-dihydro-1H-inden-1-yl)morpholine-3-carboxamide

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a 50 mL pear flask were added 4-(5-bromo-2-chloropyrimidin-4-yl)morpholine-3-carboxylic acid (PREPARATION x30, 300 mg, 0.930 mmol), 1-hydroxybenzotriazole (126 mg, 0.930 mmol), and (S)-2,3-dihydro-1H-inden-1-amine (0.119 mL, 0.930 mmol) in 1,4-dioxane (25 mL) to give a green solution. 1-Ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (178 mg, 0.930 mmol) was added to the solution, which was allowed to reaction at room temperature for 6 hours. The reaction mixture was subsequently partitioned between aqueous saturated NaHCO3 and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound, which was used without further purification. ESI-MS m/z [M+H]+ calc'd for C18H18BrClN4O2, 437.03. found 437.2.

후처리

  1. customto give a green solution
  2. customwas allowed to reaction at room temperature for 6 hours
  3. customThe reaction mixture was subsequently partitioned between aqueous saturated NaHCO3 and ethyl acetate
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-22b0c21d604d467a92348804dae3c241
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791107B2

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