Triethylamine → HCID 66681429, 화합물

HRID 339641

반응식

HRID 339641 반응식
Cl.[CH:2]1([CH2:5][NH:6][C:7](=[O:15])[CH:8]=[C:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[F:23][C:24]([F:35])([F:34])[C:25]([C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)=O.C([BH3-])#N.[Na+]>C(Cl)Cl.CO.Cl[Ti](Cl)(Cl)Cl>[CH:2]1([CH2:5][NH:6][C:7](=[O:15])[CH:8]=[C:9]2[CH2:14][CH2:13][N:12]([CH:25]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[C:24]([F:23])([F:35])[F:34])[CH2:11][CH2:10]2)[CH2:4][CH2:3]1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 695642,2,2,4'-TetrafluoroacetophenoneHCID 5003444Sodium cyanoborohydrideHCID 66680987N-(cyclopropylmethyl)-2-(piperidin-4-ylidene)acetamide hydrochloride

생성물 1

HCID 66681429HCID 66681429, 화합물수율 26%

시약·촉매·용매 3

HCID 24193Titanium Tetrachloride촉매HCID 887Methanol용매HCID 6344Dichloromethane용매2회

실험 절차

A solution of TiCl4 (0.0299 ml, 0.271 mmol) in CH2Cl2 (0.5 ml) was added to a solution of N-(cyclopropylmethyl)-2-(piperidin-4-ylidene)acetamide hydrochloride (125 mg, 0.542 mmol) prepared in EXAMPLE 22e, triethylamine (0.225 ml, 1.63 mmol) and 2,2,2,4′-tetrafluoroacetophenone (0.0770 ml, 0.542 mmol) in CH2Cl2 (3.5 ml), and the whole was stirred for 9 hours. A solution of sodium cyanoborohydride (102 mg, 1.63 mmol) in methanol (1 ml) was added to the reaction mixture and the whole was stirred for 30 minutes. After the reaction was quenched with aqueous 2 N NaOH solution (15 ml), the aqueous phase was extracted with ethyl acetate (30 ml×2) and the combined organic phase was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate/n-hexane: 35/65 to 55/45) to give N-(cyclopropylmethyl)-2-(1-(2,2,2-trifluoro-1-(4-fluorophenyl)ethyl)piperidin-4-ylidene)acetamide (52 mg, 26%) as a yellow solid: LCMS: 371 {M+1}+. 1H NMR (DMSO-d6)□ δ: 0.11 (m, 2H), 0.37 (m, 2H), 0.85 (m, 1H), 2.17 (m, 2H), 2.43-2.68 (m, 4H), 2.91 (m, 4H), 4.70 (m, 1H), 5.57 (s, 1H), 7.26 (m, 2H), 7.45 (m, 2H), 7.87 (t, 1H).

후처리

  1. stirringthe whole was stirred for 30 minutes
  2. customAfter the reaction was quenched with aqueous 2 N NaOH solution (15 ml)
  3. extractionthe aqueous phase was extracted with ethyl acetate (30 ml×2)
  4. dry with materialthe combined organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (ethyl acetate/n-hexane: 35/65 to 55/45)

출처 및 근거

ORD 기록
ord-e27e3498ea2a460abf06d6052f51e120
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895551B2

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