Methyl chloroformate → HCID 58032654, compound

HRID 1046876Notes

Reaction equation

HRID 1046876 reaction equation
[NH2:1][C:2]1[N:34]=[C:5]2[N:6]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)[C:7]([CH3:23])=[C:8]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:9]([C:10]3[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=3)[N:4]2[N:3]=1.C1COCC1.Cl[C:41]([O:43][CH3:44])=[O:42]>N1C=CC=CC=1>[C:16]([C:13]1[CH:14]=[CH:15][C:10]([CH:9]2[N:4]3[N:3]=[C:2]([NH:1][C:41]([O:43][CH3:44])=[O:42])[N:34]=[C:5]3[N:6]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:31])([F:33])[F:32])[CH:25]=3)[C:7]([CH3:23])=[C:8]2[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:11][CH:12]=1)#[N:17]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8028TetrahydrofuranHCID 66628216HCID 66628216, compound

Product 1

HCID 58032654HCID 58032654, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Under an atmosphere of argon protective gas, ethyl 2-amino-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate (10 mg, 21 μmol) was dissolved in a mixture of abs. THF (3 ml) and abs. pyridine (3 ml). At 0° C., methyl chloroformate (17 mg, 180 μmol, 8.5 eq.) was added in two portions and the mixture was stirred for 12 h with warming to RT. Once HPLC analysis showed substantial conversion, the reaction mixture was concentrated under reduced pressure and purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (10.8 mg, 96% of theory).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. custompurified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA)
  3. customAfter lyophilization, the product was obtained as a solid (10.8 mg, 96% of theory)

Sources & evidence

ORD record
ord-37a00d89119947c290188c36aad65ef1
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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