Triethylamine → 7-[(2,4-Dichloro-3-fluorophenyl)carbonyl]-3-(1H-pyrazol-1-yl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

HRID 1889101Notes

Reaction equation

[N:1]1([C:6]2[N:10]3[CH2:11][CH2:12][NH:13][CH2:14][C:9]3=[N:8][N:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.C(N(CC)CC)C.[Cl:22][C:23]1[C:31]([F:32])=[C:30]([Cl:33])[CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26].C([O-])(O)=O.[Na+]>ClCCl.C(OCC)(=O)C>[Cl:22][C:23]1[C:31]([F:32])=[C:30]([Cl:33])[CH:29]=[CH:28][C:24]=1[C:25]([N:13]1[CH2:12][CH2:11][N:10]2[C:6]([N:1]3[CH:5]=[CH:4][CH:3]=[N:2]3)=[N:7][N:8]=[C:9]2[CH2:14]1)=[O:26]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 3-(1H-pyrazol-1-yl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine (I107)(14.3 mg, 0.075 mmol) and triethylamine (0.016 ml, 0.113 mmol) was stirred in Dichloromethane (DCM) (1 ml) at 0° C. and 2,4-dichloro-3-fluorobenzoyl chloride (18.81 mg, 0.083 mmol) in DCM (0.5 ml) was added and the mixture was stirred at 0° C. After 1 h, sat. NaHCO3 (1 ml) and ethyl acetate (30 ml) were added and the product was extracted into ethyl acetate. The organic layer was dried (Na2SO4) and evaporated. Chromatography (SP4 50-100% ethyl acetate in isohexane) gave a crude product which was passed through an SCX column (elution with 2M NH3 in MeOH) to give clean desired product as a gum. This was triturated with ether/hexane to give a white solid in 22.4 mg.

Workup

extractionthe product was extracted into ethyl acetate
dry with materialThe organic layer was dried (Na2SO4)
customevaporated
customChromatography (SP4 50-100% ethyl acetate in isohexane) gave a crude product which
washwas passed through an SCX column (elution with 2M NH3 in MeOH)

Sources & evidence

ORD record: ord-ed122f7289344d6f82591bb5952739c1
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501946B2

Reaction notes

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