Dimethylformamide → HCID 136389294, compound

HRID 1161590Notes

Reaction equation

HRID 1161590 reaction equation
CN(C=O)C.C[O:7][C:8](=O)[N:9]=[C:10](SC)[C:11]([C:25]1[CH:30]=[C:29]([OH:31])[CH:28]=[C:27]([O:32][CH2:33][CH3:34])[CH:26]=1)=[N:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:23]=[C:22]([CH3:24])[O:21][N:20]=2)=[CH:15][CH:14]=1.[NH:38]([C:40]1[N:45]=[CH:44][CH:43]=[CH:42][N:41]=1)[NH2:39]>C(N(CC)CC)C>[CH2:33]([O:32][C:27]1[CH:26]=[C:25]([CH:11]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]3[N:23]=[C:22]([CH3:24])[O:21][N:20]=3)=[CH:17][CH:18]=2)[C:10]2[NH:9][C:8](=[O:7])[N:38]([C:40]3[N:45]=[CH:44][CH:43]=[CH:42][N:41]=3)[N:39]=2)[CH:30]=[C:29]([OH:31])[CH:28]=1)[CH3:34]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 3465582-HydrazinylpyrimidineHCID 72312784HCID 72312784, compound

Product 1

HCID 136389294HCID 136389294, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
85 °C

Procedure

To 1 ml of a DMF solution containing 45 mg of {2-(3-ethoxy-5-hydroxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester (Example (78a)), 11 mg of 2-hydrazinopyrimidine and 0.014 ml of triethylamine were added. The resulting mixture was stirred at 85° C. for one day under a nitrogen atmosphere and then concentrated. The residue was dissolved in 1 ml of methanol, 1 ml of THF, and 0.1 ml of acetic acid, and 100 mg of sodium cyanotrihydroborate was further added thereto. The mixture was stirred at room temperature for 3 hours. The reaction mixture was crudely purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid) to give a crude product of 5-{(3-ethoxy-5-hydroxyphenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-2-pyrimidin-2-yl-2,4-dihydro-[1,2,4]triazol-3-one.

Workup

  1. additionwere added
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in 1 ml of methanol
  4. addition1 ml of THF, and 0.1 ml of acetic acid, and 100 mg of sodium cyanotrihydroborate was further added
  5. stirringThe mixture was stirred at room temperature for 3 hours
  6. customThe reaction mixture was crudely purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid)

Sources & evidence

ORD record
ord-410070e804994464a0b86c5e43665d42
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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