1-Hydroxybenzotriazole → 1'-{[3,5-Diethoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl]carbonyl}-6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)spiro[chroman-2,4'-piperidin]-4-one

HRID 1096893ノート

反応式

HRID 1096893 の反応式
C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH2:23]([O:25][C:26]1[CH:27]=[C:28]([CH:32]=[C:33]([O:41][CH2:42][CH3:43])[C:34]=1[C:35]1[CH:36]=[N:37][N:38]([CH3:40])[CH:39]=1)[C:29]([OH:31])=O)[CH3:24].Cl.[O:45]=[C:46]1[O:50][N:49]=[C:48]([C:51]2[CH:52]=[C:53]3[C:63](=[CH:64][CH:65]=2)[O:62][C:56]2([CH2:61][CH2:60][NH:59][CH2:58][CH2:57]2)[CH2:55][C:54]3=[O:66])[NH:47]1>O.CN(C=O)C.CCN(CC)CC>[CH2:42]([O:41][C:33]1[CH:32]=[C:28]([C:29]([N:59]2[CH2:60][CH2:61][C:56]3([CH2:55][C:54](=[O:66])[C:53]4[C:63](=[CH:64][CH:65]=[C:51]([C:48]5[NH:47][C:46](=[O:45])[O:50][N:49]=5)[CH:52]=4)[O:62]3)[CH2:57][CH2:58]2)=[O:31])[CH:27]=[C:26]([O:25][CH2:23][CH3:24])[C:34]=1[C:35]1[CH:36]=[N:37][N:38]([CH3:40])[CH:39]=1)[CH3:43]

参加物

8

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 579310273,5-diethoxy-4-(1-methyl-1H-pyrazol-4-yl)benzoic acidHCID 1363426496-(5-Oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)spiro[chroman-2,4'-piperidin]-4-one hydrochloride

生成物 1

HCID 1359101731'-{[3,5-Diethoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl]carbonyl}-6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)spiro[chroman-2,4'-piperidin]-4-one

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

Et3N (58 μL), HOBT (32 mg) and WSC hydrochloride (40 mg) were added to a DMF (4 mL) solution of 3,5-diethoxy-4-(1-methyl-1H-pyrazol-4-yl)benzoic acid (50 mg) and 6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (70 mg), and stirred overnight at room temperature. Water was added to the reaction liquid, the formed solid was taken out through filtration, and the solid was fully washed with water and ether. The solid was dried under reduced pressure to obtain the title compound. 1H-NMR (400 MHz, DMSO-d6) δ: 12.96 (1H, s), 8.21 (1H, d, J=4.0 Hz), 8.06 (1H, s), 8.00 (1H, dd, J=8.0, 4.0 Hz), 7.92 (1H, s), 7.30 (1H, d, J=8.0 Hz), 6.68 (2H, s), 4.32-4.18 (1H, m), 4.08 (4H, q, J=8.0 Hz), 3.86 (3H, s), 3.64-3.20 (3H, m), 2.97 (2H, s), 2.10-1.75 (4H, m), 1.37 (6H, t, J=8.0 Hz). MS [M+H]+=574.

後処理

  1. filtrationthe formed solid was taken out through filtration
  2. washthe solid was fully washed with water and ether
  3. customThe solid was dried under reduced pressure

出典と根拠

ORDレコード
ord-6d3e4b5ab4264facbd27f9c56b3f03a0
出典データセット
uspto-grants-2012_03
特許番号
US08138197B2

反応ノート

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