1-Hydroxybenzotriazole → HCID 178425202, compound

HRID 1500981Notes

Reaction equation

HRID 1500981 reaction equation
[Br:1][C:2]1[C:3]([C:19]#[N:20])=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][C:7]=1[Cl:15].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[NH2:43][CH2:44][C:45]1[C:46]([OH:53])=[N:47][C:48]([CH3:52])=[CH:49][C:50]=1[CH3:51]>O.ClCCl.C(N(CC)CC)C>[Br:1][C:2]1[C:3]([C:19]#[N:20])=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH:43][CH2:44][C:45]2[C:46]([OH:53])=[N:47][C:48]([CH3:52])=[CH:49][C:50]=2[CH3:51])=[O:12])=[CH:8][C:7]=1[Cl:15]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69672126HCID 69672126, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425202HCID 178425202, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4-(3-bromo-2-cyanophenoxy)-3-chlorobenzoic acid (1 g, 2.8 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.08 g, 5.7 mmol), N-hydroxybenzotriazole (769 mg, 5.7 mmol), triethylamine (0.1 mL) and dichloromethane (5 mL) was stirred at 25° C. for half an hour. And then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (430 mg, 2.8 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 4-(3-bromo-2-cyanophenoxy)-3-chloro-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide as a white solid (1.1 g, 83%). LRMS (M+H+) m/z: calcd 485.01. found 485. 1H NMR (300 MHz, d6-DMSO): δ 11.44 (s, 1H), 8.52 (s, 1H), 8.12 (s, 1H), 7.90-7.87 (m, 1H), 7.61-7.52 (m, 2H), 7.37 (d, J=6.0 Hz, 1H), 6.86 (d, J=6.3 Hz, 1H), 5.82 (s, 1H), 4.25 (s, 2H), 2.45 (s, 3H), 2.40 (s, 3H).

Workup

  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)

Sources & evidence

ORD record
ord-1953e033aa2e45a59f168ea546146366
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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