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 602455ノート

反応式

HRID 602455 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2e63d05c5fa847c4bad503eeee96a9c0
出典データセット
uspto-grants-2011_03
特許番号
US07906532B2

反応ノート

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