HCID 178436776, compound → HCID 136242593, compound

HRID 1509051Notes

Reaction equation

HRID 1509051 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:12]=[C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20]/[C:21](=[N:24]\[C:25](=O)[O:26]C4C=CC=CC=4)/[NH:22][OH:23])=[CH:16][CH:15]=3)[C:10]([CH2:34][CH3:35])=[C:9]([CH3:36])[N:8]=2)=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:12]=[C:11]([NH:13][C:14]3[CH:15]=[CH:16][C:17]([CH2:20][C:21]4[NH:24][C:25](=[O:26])[O:23][N:22]=4)=[CH:18][CH:19]=3)[C:10]([CH2:34][CH3:35])=[C:9]([CH3:36])[N:8]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 178436776HCID 178436776, compound

Product 1

HCID 136242593HCID 136242593, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 50-mL round bottomed flask was charged with Phenyl (NE)-N-[2-[4-[[2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]phenyl]-1-(hydroxyamino)ethylidene)carbamate (80 mg, 0.15 mmol) and toluene (10 ml). The mixture was stirred under reflux overnight. After cooling to room temperature, the volatile material was removed under reduced pressure and the residue was purified by chromatography on silica gel using 1˜2% methanol in dichloromethane as eluent to give the title compound as a white solid (16 mg, 25% yield over two steps). MW=427.91. 1H NMR (400 MHz, DMSO-d6) δ 12.4 (brs, 1H), 8.57 (brs, 1H), 7.73 (d, J=8.4 Hz, 2H), 7.56 (d, J=3.6 Hz, 1H), 7.29 (d, J=8.4 Hz, 2H), 7.15 (d, J=3.6 Hz, 1H), 3.86 (s, 2H), 2.73 (q, J=7.6 Hz, 2H), 2.40 (s, 3H), 1.10 (t, J=7.6 Hz, 3H).

Workup

  1. temperatureunder reflux overnight
  2. customthe volatile material was removed under reduced pressure
  3. customthe residue was purified by chromatography on silica gel using 1˜2% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-12c31c8f820d46deb5df8795cbde1f92
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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