Acetic Acid → HCID 178521015, 화합물

HRID 931277노트

반응식

HRID 931277 반응식
[CH:1]1([C:4]2[CH:5]=[N:6][CH:7]=[C:8]([CH:14]=2)[C:9](=[NH:13])OCC)[CH2:3][CH2:2]1.C(O)(=O)C.C(N(CC)CC)C.Cl.Cl.[NH2:28][C:29]1[CH:30]=[CH:31][C:32]([N:36]2[CH2:41][CH2:40][CH2:39][C@@H:38]([C:42]([N:44]3[CH2:48][CH2:47][CH2:46][CH2:45]3)=[O:43])[CH2:37]2)=[N:33][C:34]=1N>C(O)C>[CH:1]1([C:4]2[CH:14]=[C:8]([C:9]3[NH:13][C:34]4=[N:33][C:32]([N:36]5[CH2:41][CH2:40][CH2:39][C@@H:38]([C:42]([N:44]6[CH2:48][CH2:47][CH2:46][CH2:45]6)=[O:43])[CH2:37]5)=[CH:31][CH:30]=[C:29]4[N:28]=3)[CH:7]=[N:6][CH:5]=2)[CH2:2][CH2:3]1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 89853752Ethyl 5-cyclopropylnicotinimidateHCID 89854051(R)-(1-(5,6-Diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochloride

생성물 1

HCID 178521015HCID 178521015, 화합물수율 5.8%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

To a solution of ethyl 5-cyclopropylnicotinimidate (0.2 g, 1.04 mmol) in ethanol was added acetic acid (0.1 mL), triethylamine (0.1 mL) and a solution of (R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochloride salt (0.4 g, 1.1 mmol) in ethanol. The reaction mixture was heated at reflux for 24 h. The solvent was removed under reduced pressure and to the resulting residue was added a saturated aqueous solution of ammonium chloride. The mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. The crude material was purified via preparative TLC to afford the title compound (0.025 g). 1H NMR (400 MHz, DMSO-d6) δ 0.85 (br s, 2H), 1.07 (d, 2H), 1.47-1.74 (m, 4H), 1.74-1.96 (m, 5H), 1.98-2.10 (m, 1H), 2.61 (br s, 2H), 2.92 (d, 2H), 3.41-3.59 (m, 2H), 4.33 (d, 1H), 4.39 (d, 1H), 6.86 (d, 1H), 7.81 (d, 1H), 8.00 (br s, 1H), 8.47 (br s, 1H), 9.05 (br s, 1H), 13.07 (br s, 1H). MS (ES+) (M+H) 417.36; LCMS retention time 3.03 min (Method S).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 24 h
  3. customThe solvent was removed under reduced pressure and to the resulting residue
  4. additionwas added a saturated aqueous solution of ammonium chloride
  5. extractionThe mixture was extracted with ethyl acetate
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customThe crude material was purified via preparative TLC

출처 및 근거

ORD 기록
ord-18c3e61935e5430d967f3ea2d2868b9d
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296745B2

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