Ethyl Acetate → ethyl 6-{[(3R)-1-(tert-butoxycarbonyl)-3-piperidinyl]amino}-5-chloronicotinate

HRID 226383

반응식

HRID 226383 반응식
[Cl:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(N(CC)C(C)C)(C)C.[NH2:23][C@@H:24]1[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]1.CCOC(C)=O>CN1CCN(C)C1=O.O>[C:33]([O:32][C:30]([N:26]1[CH2:27][CH2:28][CH2:29][C@@H:24]([NH:23][C:3]2[C:2]([Cl:1])=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]=2)[CH2:25]1)=[O:31])([CH3:36])([CH3:34])[CH3:35]

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylateHCID 16762519Ethyl 5,6-Dichloronicotinate

생성물 1

HCID 68960873ethyl 6-{[(3R)-1-(tert-butoxycarbonyl)-3-piperidinyl]amino}-5-chloronicotinate

시약·촉매·용매 2

HCID 962Water용매HCID 66611,3-Dimethyl-2-imidazolidinone용매

반응 조건

온도
100 °C

실험 절차

To a solution of ethyl 5,6-dichloronicotinate (10.0 g) and N,N-diisopropylethylamine (17.4 mL) in 1,3-dimethyl-2-imidazolidinone (100 mL) was added tert-butyl (3R)-3-amino-1-piperidinecarboxylate (10.9) at ambient temperature and the mixture was stirred at 100° C. for 9 hr. The reaction mixture was poured into a mixture of AcOEt and water. The separated organic layer was added ice-water and the mixture was adjusted to pH 3.5 with 1N-NCl. The separated organic layer was washed with water, dried over magnesium sulfate and evaporated in vacuo to give ethyl 6-{[(3R)-1-(tert-butoxycarbonyl)-3-piperidinyl]amino}-5-chloronicotinate (16.74 g).

후처리

  1. washThe separated organic layer was washed with water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-189540655c5b42c18e5e1e88f126e5c4
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557127B2

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