Diethyl cyanophosphonate → tert-Butyl cis-2-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]-5-{[(1-isopropyl-1H-indazol-3-yl)carbonyl]amino}piperidine-1-carboxylate

HRID 602455노트

반응식

HRID 602455 반응식
[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([OH:15])=O)=[N:5]1)([CH3:3])[CH3:2].[NH2:16][C@H:17]1[CH2:22][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@@H:20]([CH2:30][C:31]2([OH:37])[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[CH2:19][CH2:18]1.C(N(CC)C(C)C)(C)C.C(P(=O)(OCC)OCC)#N>CN(C)C=O>[OH:37][C:31]1([CH2:30][C@H:20]2[CH2:19][CH2:18][C@@H:17]([NH:16][C:13]([C:6]3[C:7]4[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=4)[N:4]([CH:1]([CH3:2])[CH3:3])[N:5]=3)=[O:15])[CH2:22][N:21]2[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1

참가 물질

6

반응물 4

HCID 76257Diethyl cyanophosphonateHCID 81531DiisopropylethylamineHCID 106796951-Isopropyl-1H-indazole-3-carboxylic acidHCID 67269815tert-Butyl cis-5-amino-2-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]piperidine-1-carboxylate

생성물 1

HCID 67270163tert-Butyl cis-2-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]-5-{[(1-isopropyl-1H-indazol-3-yl)carbonyl]amino}piperidine-1-carboxylate수율 94.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 1-isopropyl-1H-indazole-3-carboxylic acid (126 mg, 0.619 mmol), tert-butyl cis-5-amino-2-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]piperidine-1-carboxylate (234 mg, 0.743 mmol, step 5 of Example 2), N,N-diisopropylethylamine (96 mg, 0.743 mmol) in N,N-dimethylformamide (3 mL) was added diethyl cyanophosphonate (121 mg, 0.743 mmol) at room temperature, and the mixture was stirred at the same temperature for 18 h. The mixture was concentrated under reduced pressure and the resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (1:1) to give 292 mg (94%) of the title compound as a colorless oil.

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (1:1)

출처 및 근거

ORD 기록
ord-2e63d05c5fa847c4bad503eeee96a9c0
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906532B2

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