Water → HCID 76071651, compound

HRID 1778203Notes

Reaction equation

HRID 1778203 reaction equation
[CH3:1][C:2]1[N:6]2[CH:7]=[C:8]([CH:13]=O)[N:9]=[C:10]([NH:11][CH3:12])[C:5]2=[N:4][N:3]=1.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O[N:24]=[C:25]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:26](=O)[CH3:27].O>C(O)(=O)C>[CH2:15]([N:22]1[C:26]([CH3:27])=[C:25]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:24]=[C:13]1[C:8]1[N:9]=[C:10]([NH:11][CH3:12])[C:5]2[N:6]([C:2]([CH3:1])=[N:3][N:4]=2)[CH:7]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 6708483HCID 6708483, compoundHCID 86719152HCID 86719152, compound

Product 1

HCID 76071651HCID 76071651, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

3-Methyl-8-methylamino-[1,2,4]-triazolo[4,3-a]pyrazine-6-carbaldehyde (34 mg; 0.18 mmol), benzylamine (20 μl; 0.18 mmol) and 1-hydroxyimino-1-phenyl-propan-2-one (32 mg; 0.18 mmol) are dissolved in 0.6 ml acetic acid stirred for 2 h at 120° C. The reaction mixture is treated with water and extracted with DCM. The organic layer is dried over MgSO4 and evaporated to dryness. The crude intermediate is dissolved in 20 ml of THF and treated with Ra—Ni. The reaction mixture is stirred for 2 days at 25° C. and 4 bar hydrogen atmosphere. The solid materials are filtered off and the crude product is purified using reversed phase chromatography (Method: prep. HPLC1).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic layer is dried over MgSO4
  3. customevaporated to dryness
  4. dissolutionThe crude intermediate is dissolved in 20 ml of THF
  5. additiontreated with Ra—Ni
  6. stirringThe reaction mixture is stirred for 2 days at 25° C.
  7. filtrationThe solid materials are filtered off
  8. customthe crude product is purified

Sources & evidence

ORD record
ord-5e30ec331a194eadb1307dd69242d036
Source dataset
uspto-grants-2016_02
Patent number
US09266891B2

Reaction notes

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