Triethylamine → 2-Benzyl-5-(4-cyanophenyl)-7-methyl-3-oxo-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylic acid methyl ester

HRID 570868Notes

Reaction equation

[N+](C1C=CC(O[C:11]([N:13]2[CH:18]([C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=3)[C:17]([C:27]([O:29][CH3:30])=[O:28])=[C:16]([CH3:31])[N:15]=[C:14]2OC)=[O:12])=CC=1)([O-])=O.Cl.[CH2:35]([NH:42][NH2:43])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.CCN(CC)CC>CC#N>[CH3:30][O:29][C:27]([C:17]1[CH:18]([C:19]2[CH:20]=[CH:21][C:22]([C:25]#[N:26])=[CH:23][CH:24]=2)[N:13]2[C:11](=[O:12])[N:42]([CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:43]=[C:14]2[NH:15][C:16]=1[CH3:31])=[O:28]

Participants

Conditions

Temperature: 0 °C

Procedure

Intermediate 5 (250 mg, 0.55 mmol) and benzyl hydrazine hydrochloride (120 mg, 0.61 mmol) were suspended in CH3CN (10 mL) at 0° C., and Et3N (85 μl, 0.61 mmol) was added. The reaction mixture was stirred at 0° C. for 30 mins and then allowed to reach RT and stirred for a further 1 hour. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The resulting residue was purified by silica gel chromatography eluting with a gradient of 0-100% to yield the title compound as a yellow solid (100 mg).

Workup

customto reach RT
stirringstirred for a further 1 hour
filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated in vacuo
customThe resulting residue was purified by silica gel chromatography
washeluting with a gradient of 0-100%

Sources & evidence

ORD record: ord-9d53a47cd66a473a987b976aa878eadc
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023855B2

Reaction notes

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