Ammonia → 6-Phenyl-5-(4-{[4-(5-pyridin-2-yl-1H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)[1,2,4]triazolo[1,5-a]pyrimidin-2-amine

HRID 1915610Notes

Reaction equation

HRID 1915610 reaction equation
C([C:3]1[N:41]=[C:6]2[N:7]=[C:8]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][N:24]4[CH2:29][CH2:28][CH:27]([C:30]5[N:34]=[C:33](C6C=CC=CN=6)[NH:32][N:31]=5)[CH2:26][CH2:25]4)=[CH:19][CH:18]=3)[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:10][N:5]2[N:4]=1)#C.[NH3:42].[CH2:43](O)[CH3:44]>C1COCC1>[C:11]1([C:9]2[C:8]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][N:24]4[CH2:29][CH2:28][CH:27]([C:30]5[N:34]=[C:33]([C:44]6[CH:43]=[CH:8][CH:9]=[CH:10][N:5]=6)[NH:32][N:31]=5)[CH2:26][CH2:25]4)=[CH:19][CH:18]=3)=[N:42][C:6]3[N:5]([N:4]=[C:3]([NH2:41])[N:7]=3)[CH:10]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 702EthanolHCID 178437545HCID 178437545, compound

Product 1

HCID 1785082456-Phenyl-5-(4-{[4-(5-pyridin-2-yl-1H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)[1,2,4]triazolo[1,5-a]pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
140 °C

Procedure

To 500 mg 2-bromo-6-phenyl-5-(4-{[4-(5-pyridin-2-yl-1H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)[1,2,4]triazolo[1,5-a]pyrimidine (prepared as described under example 53) in 3 ml THF and 5 ml ethanol are added 8 ml of a ammonia solution (25% in water). The reaction mixture is heated to 140° C. for 22 hours. The solvent is evaporated and the solid residue is stirred in diethyl ether/ethanol (9:1). The product is filtrated, dried and further purified by RP HPLC (water, 10 mM NH4COOH, pH 3.7/ACN) to yield the desired compound.

Workup

  1. customThe solvent is evaporated
  2. filtrationThe product is filtrated
  3. customdried
  4. customfurther purified by RP HPLC (water, 10 mM NH4COOH, pH 3.7/ACN)

Sources & evidence

ORD record
ord-bee6e34f70cc4f228f3ae3a0f28b59a1
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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