Hydrazine → HCID 178482365, compound

HRID 252641Notes

Reaction equation

HRID 252641 reaction equation
[C:1]([NH:9][C:10](=[N:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[C:26]([C:27]3[CH:32]=[CH:31][N:30]=[C:29]([NH:33][CH3:34])[N:28]=3)=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:16][CH:15]=1)SC)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:35][NH2:36]>CCO>[CH3:34][NH:33][C:29]1[N:28]=[C:27]([C:26]2[C:21]([O:20][C:17]3[CH:18]=[CH:19][C:14]([NH:13][C:10]4[NH:9][C:1]([C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)=[N:36][N:35]=4)=[CH:15][CH:16]=3)=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:32]=[CH:31][N:30]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 136367426HCID 136367426, compound

Product 1

HCID 178482365HCID 178482365, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A slurry of 1-benzoyl-2-methyl-3-(4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)isothiourea (0.174 g, 0.37 mmol) and anhydrous hydrazine (0.35 ml, 11 mmol) in EtOH was sealed and heated to 80° C. After 16 h, a yellow precipitate formed. The reaction was cooled to ambient temperature, filtered, rinsing with 2×1 mL EtOH, and the solid was dried in vacuo to give N-methyl-4-(2-(4-(5-phenyl-4H-1,2,4-triazol-3-ylamino)phenoxy)pyridin-3-yl)pyrimidin-2-amine as a white solid. MS m/z=437 [M+H]+. Calc'd for C24H20N8O: 436.5.

Workup

  1. customa yellow precipitate formed
  2. temperatureThe reaction was cooled to ambient temperature
  3. filtrationfiltered
  4. washrinsing with 2×1 mL EtOH
  5. customthe solid was dried in vacuo

Sources & evidence

ORD record
ord-5f78136ca55042b0baa5551d03b750d9
Source dataset
uspto-grants-2011_01
Patent number
US07868177B2

Reaction notes

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