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1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 6-[(1-methyl-1H-pyrazol-5-yl)amino]-1'-{[2-phenyl-6-(tetrazol-5-yl)pyridin-4-yl]carbonyl}spiro[chroman-2,4'-piperidin]-4-one

HRID 1096884
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HRID 1096884 반응식
Cl.[CH3:2][N:3]1[C:7]([NH:8][C:9]2[CH:10]=[C:11]3[C:21](=[CH:22][CH:23]=2)[O:20][C:14]2([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH2:13][C:12]3=[O:24])=[CH:6][CH:5]=[N:4]1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[C:48]1([C:54]2[CH:55]=[C:56]([CH:60]=[C:61]([C:63]3[NH:67][N:66]=[N:65][N:64]=3)[N:62]=2)[C:57](O)=[O:58])[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>O.CN(C=O)C.C(N(CC)CC)C>[CH3:2][N:3]1[C:7]([NH:8][C:9]2[CH:10]=[C:11]3[C:21](=[CH:22][CH:23]=2)[O:20][C:14]2([CH2:15][CH2:16][N:17]([C:57]([C:56]4[CH:60]=[C:61]([C:63]5[NH:67][N:66]=[N:65][N:64]=5)[N:62]=[C:54]([C:48]5[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=5)[CH:55]=4)=[O:58])[CH2:18][CH2:19]2)[CH2:13][C:12]3=[O:24])=[CH:6][CH:5]=[N:4]1
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참가 물질

8

반응물 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 666494456-[(1-Methyl-1H-pyrazol-5-yl)amino]spiro[chroman-2,4'-piperidin]-4-one hydrochlorideHCID 1785241162-Phenyl-6-(tetrazol-5-yl)-isonicotinic acid

생성물 1

HCID 178481810
6-[(1-methyl-1H-pyrazol-5-yl)amino]-1'-{[2-phenyl-6-(tetrazol-5-yl)pyridin-4-yl]carbonyl}spiro[chroman-2,4'-piperidin]-4-one

시약·촉매·용매 3

HCID 962Water용매2회HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

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온도
60 °C

실험 절차

6-[(1-Methyl-1H-pyrazol-5-ylamino)]spiro[chroman-2,4′-piperidin]-4-one hydrochloride (117 mg), 1-hydroxybenzotriazole monohydrate (53 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (68 mg), triethylamine (94 μL) and water (1 mL) were added in that order to a DMF (3 mL) solution of 2-phenyl-6-(tetrazol-5-yl)-isonicotinic acid (75 mg), and stirred at 60° C. for 1 hour. Water was added to the reaction liquid, and the resulting precipitate was taken out through filtration, washed with hexane/ethyl acetate=2/1, and dried to obtain the title compound as a yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ: 8.37 (2.0H, d, J=6.8 Hz), 8.17 (1.0H, s), 8.08 (1.0H, br s), 7.93 (1.0H, s), 7.61-7.50 (3.0H, m), 7.32 (1.0H, d, J=2.0 Hz), 7.18-7.12 (2.0H, m), 6.99 (1.0H, d, J=8.4 Hz), 5.89 (1.0H, s), 4.31-4.27 (1.0H, m), 3.60 (3.0H, s), 3.50-3.20 (3.0H, m), 2.82 (2.0H, s), 2.12-2.05 (1.0H, m), 1.90-1.78 (3.0H, m). MS [M−H]+=560.

후처리

  1. filtrationthe resulting precipitate was taken out through filtration
  2. washwashed with hexane/ethyl acetate=2/1
  3. customdried

출처 및 근거

ORD 기록
ord-d689236cf06942adad4783e953726409
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08138197B2

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