Diisopropylethylamine → 2-Allyl-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 570869Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)[N:7]=[C:8](OC)[NH:9][C:10]=1[CH3:11])=[O:4].Cl[C:23](OC1C=CC([N+]([O-])=O)=CC=1)=[O:24].Cl.[CH2:36]([NH:39][NH2:40])[CH:37]=[CH2:38].CCN(C(C)C)C(C)C>C(Cl)Cl.N1C=CC=CC=1.CC#N>[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:14]2[CH:15]=[CH:16][C:17]([C:20]#[N:21])=[CH:18][CH:19]=2)[N:7]2[C:23](=[O:24])[N:39]([CH2:36][CH:37]=[CH2:38])[N:40]=[C:8]2[NH:9][C:10]=1[CH3:11])=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

Intermediate 4 (1.42 g, 5 mmol) was dissolved in a mixture of DCM (10 mL) and pyridine (10 mL) and cooled using an ice bath. A solution of 4-nitrophenyl chloroformate (0.955 mg, 4.75 mmol) in DCM (10 mL) was added dropwise, and the resulting solution was stirred at 0° C. for 1.5 hours, and then a solution of allyl hydrazine hydrochloride (1.0 g, 5.5 mmol) and DIPEA (3.75 mL, 22 mmol) in CH3CN (10 mL) was added in one portion. The resulting mixture was allowed to warm to RT, stirred for 4 hours, and then partitioned between EtOAc and water. The organic layer was separated, washed with water, followed by brine, then dried (Na2SO4) and evaporated in vacuo to yield the title compound as a yellow oil (0.95 g).

Workup

temperaturecooled
temperatureto warm to RT
stirringstirred for 4 hours
custompartitioned between EtOAc and water
customThe organic layer was separated
washwashed with water
dry with materialdried (Na2SO4)
customevaporated in vacuo

Sources & evidence

ORD record: ord-18faef08bed543908b2ad9155e659056
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023855B2

Reaction notes

Loading…