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1-Hydroxybenzotriazole → 6-(5-bromopyridin-3-yl)-1'-[(1-cyclopropyl-4-methoxy-3-methyl-1H-indol-6-yl)carbonyl]spiro[chroman-2,4'-piperidin]-4-one

HRID 420132
ノート
印刷プレビュー

反応式

HRID 420132 の反応式
[CH:1]1([N:4]2[C:12]3[C:7](=[C:8]([O:16][CH3:17])[CH:9]=[C:10]([C:13]([OH:15])=O)[CH:11]=3)[C:6]([CH3:18])=[CH:5]2)[CH2:3][CH2:2]1.Cl.Cl.[Br:21][C:22]1[CH:23]=[C:24]([C:28]2[CH:29]=[C:30]3[C:40](=[CH:41][CH:42]=2)[O:39][C:33]2([CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH2:32][C:31]3=[O:43])[CH:25]=[N:26][CH:27]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>C(OCC)(=O)C.CN(C=O)C.C(N(CC)CC)C>[Br:21][C:22]1[CH:23]=[C:24]([C:28]2[CH:29]=[C:30]3[C:40](=[CH:41][CH:42]=2)[O:39][C:33]2([CH2:34][CH2:35][N:36]([C:13]([C:10]4[CH:11]=[C:12]5[C:7]([C:6]([CH3:18])=[CH:5][N:4]5[CH:1]5[CH2:2][CH2:3]5)=[C:8]([O:16][CH3:17])[CH:9]=4)=[O:15])[CH2:37][CH2:38]2)[CH2:32][C:31]3=[O:43])[CH:25]=[N:26][CH:27]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 569716581-cyclopropyl-4-methoxy-3-methyl-1H-indole-6-carboxylic acidHCID 666493846-(5-Bromo-3-pyridinyl)spiro-[chroman-2,4'-piperidin]-4-one dihydrochloride

生成物 1

HCID 24966800
6-(5-bromopyridin-3-yl)-1'-[(1-cyclopropyl-4-methoxy-3-methyl-1H-indol-6-yl)carbonyl]spiro[chroman-2,4'-piperidin]-4-one

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Triethylamine (0.33 mL) was added to a DMF (7.5 mL) solution of 1-cyclopropyl-4-methoxy-3-methyl-1H-indole-6-carboxylic acid (147 mg), 6-(5-bromo-3-pyridinyl)spiro-[chroman-2,4′-piperidin]-4-one dihydrochloride (268 mg), WSC hydrochloride (164 mg) and HOBT (110 mg), and stirred at r.t. for 5 h. This reaction mixture was diluted with ethyl acetate, then washed with water, aqueous saturated sodium bicarbonate and saturated saline water in that order, and dried with sodium sulfate. This was filtered, concentrated, and purified through silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound as a colorless amorphous substance. 1H-NMR (400 MHz, DMSO-d6) δ: 8.86 (1H, d, J=2.0 Hz), 8.66 (1H, d, J=2.0 Hz), 8.36 (1H, t, J=2.0 Hz), 8.05-7.99 (2H, m), 7.24 (1H, d, J=8.6 Hz), 7.13 (1H, s), 7.00 (1H, s), 6.50 (1H, s), 4.40-4.08 (1H, br m), 3.83 (3H, s), 3.78-3.22 (4H, br m), 2.94 (2H, s), 2.31 (3H, s), 2.04-1.75 (4H, br m), 1.03-0.97 (2H, m), 0.89-0.84 (2H, m); MS [M+H]+=600, 602.

後処理

  1. washwashed with water, aqueous saturated sodium bicarbonate and saturated saline water in that order
  2. dry with materialdried with sodium sulfate
  3. filtrationThis was filtered
  4. concentrationconcentrated
  5. custompurified through silica gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-7333ecd556b34a4a942bb2c83a270d25
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08093389B2

反応ノート

読み込み中…

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