Sodium Hydroxide → 4-{[4-(2-Methyl-thiazol-4-ylmethoxy)-1H-indole-2-carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester

HRID 2267910노트

반응식

HRID 2267910 반응식
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8][C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[C:12]([C:18]([OH:20])=O)[NH:13]3)[N:6]=1.CC[N:23](C(C)C)C(C)C.[C:30]([O:34][C:35](=[O:43])NC1CCNCC1)([CH3:33])([CH3:32])[CH3:31].C1CN([P+](ON2N=[N:68][C:63]3[CH:64]=[CH:65][CH:66]=[CH:67]C2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[OH-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[C:30]([O:34][C:35]([N:68]1[CH2:63][CH2:64][CH:65]([NH:23][C:18]([C:12]2[NH:13][C:14]3[C:10]([CH:11]=2)=[C:9]([O:8][CH2:7][C:5]2[N:6]=[C:2]([CH3:1])[S:3][CH:4]=2)[CH:17]=[CH:16][CH:15]=3)=[O:20])[CH2:66][CH2:67]1)=[O:43])([CH3:33])([CH3:32])[CH3:31]

참가 물질

8

반응물 5

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 7238334-(N-Boc-amino)piperidineHCID 2724699PyBOPHCID 668416854-(2-Methyl-thiazol-4-ylmethoxy)-1H-indole-2-carboxylic acid

생성물 1

HCID 668415664-{[4-(2-Methyl-thiazol-4-ylmethoxy)-1H-indole-2-carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

4-(2-Methyl-thiazol-4-ylmethoxy)-1H-indole-2-carboxylic acid (170) (1.21 g, 4.2 mmol) is dissolved in 10 ml of DMF and the solution is cooled to 0° C. After addition of Huenigs base (2.16 ml, 12.6 mmol), piperidin-4-yl-carbamic acid tert-butyl ester (3) (841 mg, 4.2 mmol) and PyBOP (2.4 g, 4.6 mmol) the mixture is stirred at room temperature for 18 h. Ethyl acetate is added followed by concentrated sodium hydroxide, until a pH of 11 is reached. The organic layer is washed with brine, dried over sodium sulphate and evaporated under reduced pressure. The crude product is purified by flash-chromatography (silica gel, ethyl acetate/cyclohexane 1:1).

후처리

  1. washThe organic layer is washed with brine
  2. dry with materialdried over sodium sulphate
  3. customevaporated under reduced pressure
  4. customThe crude product is purified by flash-chromatography (silica gel, ethyl acetate/cyclohexane 1:1)

출처 및 근거

ORD 기록
ord-92b40e5319c64550bdb3ac8210136250
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858781B2

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