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1-Hydroxybenzotriazole → [5-(1'-{[3,5-Diethoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl]carbonyl}-4-oxospiro[chroman-2,4'-piperidin]-6-yl)-2H-tetrazol-2-yl]methyl 2,2-dimethylpropanoate

HRID 1096900
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HRID 1096900 반응식
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.[CH3:45][C:46]([CH3:73])([CH3:72])[C:47]([O:49][CH2:50][N:51]1[N:55]=[N:54][C:53]([C:56]2[CH:57]=[C:58]3[C:68](=[CH:69][CH:70]=2)[O:67][C:61]2([CH2:66][CH2:65][NH:64][CH2:63][CH2:62]2)[CH2:60][C:59]3=[O:71])=[N:52]1)=[O:48]>O.CN(C=O)C.CCN(CC)CC>[CH3:45][C:46]([CH3:73])([CH3:72])[C:47]([O:49][CH2:50][N:51]1[N:55]=[N:54][C:53]([C:56]2[CH:57]=[C:58]3[C:68](=[CH:69][CH:70]=2)[O:67][C:61]2([CH2:62][CH2:63][N:64]([C:29]([C:28]4[CH:32]=[C:33]([O:41][CH2:42][CH3:43])[C:34]([C:35]5[CH:36]=[N:37][N:38]([CH3:40])[CH:39]=5)=[C:26]([O:25][CH2:23][CH3:24])[CH:27]=4)=[O:31])[CH2:65][CH2:66]2)[CH2:60][C:59]3=[O:71])=[N:52]1)=[O:48]
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참가 물질

8

반응물 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 66781586[5-(4-Oxospiro[chroman-2,4'-piperidin]-6-yl)-tetrazol-2-yl]methyl 2,2-dimethylpropanoate hydrochloride

생성물 1

HCID 57930917
[5-(1'-{[3,5-Diethoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl]carbonyl}-4-oxospiro[chroman-2,4'-piperidin]-6-yl)-2H-tetrazol-2-yl]methyl 2,2-dimethylpropanoate

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

Et3N (223 μL), HOBT (123 mg) and WSC hydrochloride (154 mg) were added to a DMF (8 mL) solution of 3,5-diethoxy-4-(1-methyl-1H-pyrazol-4-yl)benzoic acid (194 mg) and [5-(4-oxospiro[chroman-2,4′-piperidin]-6-yl)-2H-tetrazol-2-yl]methyl 2,2-dimethylpropanoate hydrochloride (349 mg), and stirred overnight at room temperature. The reaction liquid was poured into saturated saline water, extracted with ethyl acetate, and the organic layer was washed with water and saturated saline water. The organic layer was dried with sodium sulfate, filtered, concentrated, and purified through silica gel column chromatography (hexane/EtOAc) to obtain the title compound. 1H-NMR (400 MHz, CDCl3) δ: 8.69 (1H, d, J=4.0 Hz), 8.32 (1H, dd, J=8.0, 4.0 Hz), 8.14 (1H, s), 7.97 (1H, s), 7.17 (1H, d, J=8.0 Hz), 6.64 (2H, s), 6.50 (2H, s), 4.32-4.18 (1H, m), 4.08 (4H, q, J=8.0 Hz), 3.94 (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), 1.22 (9H, s). MS [M+H]+=672.

후처리

  1. customThe reaction liquid
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with water and saturated saline water
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified through silica gel column chromatography (hexane/EtOAc)

출처 및 근거

ORD 기록
ord-c850474617cd41c8aebe2dc54e492ed6
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08138197B2

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