4-Phenoxybenzoic acid → HCID 178432752, compound

HRID 1501105Notes

Reaction equation

HRID 1501105 reaction equation
[O:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[NH2:39][CH2:40][C:41]1[C:42]([OH:49])=[N:43][C:44]([CH3:48])=[N:45][C:46]=1[CH3:47]>ClCCl.C(N(CC)CC)C>[OH:49][C:42]1[C:41]([CH2:40][NH:39][C:12](=[O:14])[C:11]2[CH:10]=[CH:9][C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:16][CH:15]=2)=[C:46]([CH3:47])[N:45]=[C:44]([CH3:48])[N:43]=1

Participants

7

Reactant 4

HCID 751824-Phenoxybenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178432754HCID 178432754, compound

Product 1

HCID 178432752HCID 178432752, compoundYield 21.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4-phenoxybenzoic acid (92 mg, 0.43 mmol), 1-hydroxybenzotriazole (80 mg, 0.6 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (113 mg, 0.6 mmol), triethylamine (0.16 mL) and dichloromethane (15 mL) was stirred at 25° C. for half an hour. Then 5-(aminomethyl)-2,6-dimethylpyrimidin-4-ol (60 mg, 0.4 mmol) was added. The mixture was stirred at 25° C. for 12 hours and then concentrated to give a residue. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1) to give N-((4-hydroxy-2,6-dimethylpyrimidin-5-yl)methyl)-4-phenoxybenzamide as a white solid (30 mg, 21%). LRMS (M+H+) m/z: calcd 349.14. found 349. HPLC purity (214 nm): 98%. 1H NMR (300 MHz, d6-DMSO): δ 12.36 (s, 1H), 8.35 (t, J=4.5 Hz, 1H), 7.86 (d, J=8.4 Hz, 2H), 7.42 (t, J=8.4 Hz, 2H), 7.24-6.97 (m, 5H), 4.25 (d, J=4.5 Hz, 2H), 2.29 (s, 3H), 2.20 (s, 3H).

Workup

  1. stirringThe mixture was stirred at 25° C. for 12 hours
  2. concentrationconcentrated
  3. customto give a residue
  4. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1)

Sources & evidence

ORD record
ord-73974949222941178d948df2bf28dceb
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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