1H-Benzotriazole, 1-hydroxy-, ammonium salt (1:1) → HCID 178425239, 화합물

HRID 2206463노트

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HRID 2206463 반응식
[CH3:1][C:2]1[N:6]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]([OH:17])=O.Cl.C(N=C=NCCCN(C)C)C.C1C=C2N=NN(O)C2=CC=1.N.[NH2:41][CH2:42][C:43]1[C:44]([OH:51])=[N:45][C:46]([CH3:50])=[CH:47][C:48]=1[CH3:49]>O.ClCCl.C(N(CC)CC)C>[OH:51][C:44]1[C:43]([CH2:42][NH:41][C:15]([C:3]2[CH:4]=[N:5][N:6]([CH2:7][CH2:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:2]=2[CH3:1])=[O:17])=[C:48]([CH3:49])[CH:47]=[C:46]([CH3:50])[N:45]=1

참가 물질

8

반응물 4

HCID 1131751H-Benzotriazole, 1-hydroxy-, ammonium salt (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22227947HCID 22227947, 화합물HCID 178425242HCID 178425242, 화합물

생성물 1

HCID 178425239HCID 178425239, 화합물수율 31%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

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온도
25 °C

실험 절차

A mixture of 5-methyl-1-phenethyl-1H-pyrazole-4-carboxylic acid (60 mg, 0.27 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (95 mg, 0.5 mmol), N-hydroxybenzotrizole (67 mg, 0.5 mmol), triethylamine (0.1 mL) and dichloromethane (5 mL) were stirred at 25° C. for 0.5 hours. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (50 mg, 0.33 mmol) was added. The mixture was stirred at 25° C. for 12 hours. To the mixture, water (10 ml) was added and the mixture was extracted with dichloromethane (10 mL t 3). The combined organic phase was dried by sodium sulfate and then filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-5-methyl-1-phenethyl-1H-pyrazole-4-carboxamide as a white solid (30 mg, 31%). LRMS (M++) m/z: calcd 364.19. found 364. 1H NMR (300 MHz, d6-DMSO): δ 11.47 (s, 1H), 8.08 (s, 1H), 7.57 (t, J=5.1 Hz, 1H), 7.30-7.15 (m, 5H), 5.85 (s, 1H), 4.23-4.18 (m, 4H), 3.06 (t, J=7.2 Hz, 2H), 2.31 (s, 3H), 2.15 (s, 3H), 2.11 (s, 3H).

후처리

  1. stirringThe mixture was stirred at 25° C. for 12 hours
  2. extractionthe mixture was extracted with dichloromethane (10 mL t 3)
  3. dry with materialThe combined organic phase was dried by sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1)

출처 및 근거

ORD 기록
ord-6c0f921e0f454652a73c9aac8195938d
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371331B2

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