1H-Benzotriazole, 1-hydroxy-, ammonium salt (1:1) → HCID 178425237、化合物

HRID 1526945ノート

反応式

HRID 1526945 の反応式
[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([C:14]([OH:16])=O)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(N=C=NCCCN(C)C)C.C1C=C2N=NN(O)C2=CC=1.N.[NH2:40][CH2:41][C:42]1[C:43]([OH:50])=[N:44][C:45]([CH3:49])=[CH:46][C:47]=1[CH3:48]>O.ClCCl.C(N(CC)CC)C>[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([C:14]([NH:40][CH2:41][C:42]2[C:43]([OH:50])=[N:44][C:45]([CH3:49])=[CH:46][C:47]=2[CH3:48])=[O:16])[CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

8

反応物 4

HCID 1131751H-Benzotriazole, 1-hydroxy-, ammonium salt (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 64931761-benzyl-5-methyl-1H-pyrazole-4-carboxylic acidHCID 178425242HCID 178425242、化合物

生成物 1

HCID 178425237HCID 178425237、化合物収率 30.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

反応条件

温度
25 °C

実験手順

A mixture of 1-benzyl-5-methyl-1H-pyrazole-4-carboxylic acid (75 mg, 0.34 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×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 1-benzyl-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-5-methyl-1H-pyrazole-4-carboxamide as a white solid (35 mg, 29%). LRMS (M+H+) m/z: calcd 350.17; found 350. 1H NMR (300 MHz, d6-DMSO): δ 11.46 (s, 1H), 8.21 (s, 1H), 7.68 (t, J=5.1 Hz, 1H), 7.38-7.21 (m, 5H), 5.85 (s, 1H), 5.20 (s, 2H), 4.19 (d, J=5.4 Hz, 2H), 2.29 (s, 3H), 2.15 (s, 3H), 2.10 (s, 3H).

後処理

  1. stirringThe mixture was stirred at 25° C. for 12 hours
  2. extractionthe mixture was extracted with dichloromethane (10 mL×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)

出典と根拠

ORDレコード
ord-f2918919741f4d07bcfc1bfb7b075777
出典データセット
uspto-grants-2015_07
特許番号
US09085583B2

反応ノート

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