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1-Hydroxybenzotriazole → N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(pentan-2-yl)benzamide

HRID 1479716
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HRID 1479716 반응식
[CH3:1][CH:2]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[NH2:37][CH2:38][C:39]1[C:40]([OH:47])=[N:41][C:42]([CH3:46])=[CH:43][C:44]=1[CH3:45]>ClCCl.C(N(CC)CC)C>[OH:47][C:40]1[C:39]([CH2:38][NH:37][C:10](=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([CH:2]([CH2:3][CH2:4][CH3:5])[CH3:1])=[CH:14][CH:13]=2)=[C:44]([CH3:45])[CH:43]=[C:42]([CH3:46])[N:41]=1
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참가 물질

7

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 2812844-(Pentan-2-yl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178425242HCID 178425242, 화합물

생성물 1

HCID 178442161N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(pentan-2-yl)benzamide수율 40%

시약·촉매·용매 2

HCID 6344
Dichloromethane
용매
HCID 8471Triethylamine용매

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온도
25 °C

실험 절차

A mixture of 4-(pentan-2-yl)benzoic acid (192 mg, 1.0 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (288 mg, 1.5 mmol), 1-hydroxybenzotriazole t (202 mg, 1.5 mmol), triethylamine (0.5 mL) and dichloromethane (15.0 mL) was stirred at 25° C. for half an hour. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (152 mg, 1.0 mmol) was added to the above mixture. The mixture was stirred at 25° C. for 12 hours. The mixture was washed with water (20 ml×2). The organic phase was dried by sodium sulphate. The mixture was filtered. The filtrate was concentrated and the residue was purified by column chromatography (silica gel, dichloromethane/methane=10:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(pentan-2-yl)benzamide as a white solid (100 mg, 40%). LRMS (M+H+) m/z: 326.2. found 326. 1H NMR (300 MHz, d6-DMSO): δ 11.46 (s, 1H), 8.26 (t, J=4.5 Hz, 1H), 7.75 (d, J=8.1 Hz, 2H), 7.23 (m, J=8.1 Hz, 2H), 5.85 (s, 1H), 4.29 (d, J=4.5 Hz, 2H), 2.76-2.69 (m, 1H), 2.17 (s, 3H), 2.11 (s, 3H), 1.54-1.47 (m, 2H), 1.18-1.05 (m, 5H), 0.81 (t, J=14.4 Hz, 3H).

후처리

  1. stirringThe mixture was stirred at 25° C. for 12 hours
  2. washThe mixture was washed with water (20 ml×2)
  3. dry with materialThe organic phase was dried by sodium sulphate
  4. filtrationThe mixture was filtered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by column chromatography (silica gel, dichloromethane/methane=10:1)

출처 및 근거

ORD 기록
ord-d5d6795cea494424b86af2faf6afc069
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09409865B2

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