Benzyl chloroformate → HCID 58032592, compound

HRID 2200977Notes

Reaction equation

HRID 2200977 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.Cl[C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37]>N1C=CC=CC=1>[CH2:39]([O:38][C:36]([NH: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:31])([F:33])[F:32])[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)=[O:37])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 66628216HCID 66628216, compound

Product 1

HCID 58032592HCID 58032592, 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 (130 mg, 278 μmol) was dissolved in abs. pyridine (3.6 ml). At 0° C., benzyl chloroformate (379 mg, 2.2 mmol, 8 eq.) was added in four 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 the residue was taken up in acetonitrile, acidified with 1 N hydrochloric acid and then 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 (146.3 mg, 87% 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 (146.3 mg, 87% of theory)

Sources & evidence

ORD record
ord-7bc8e3e3a73c41b4825237f9d95f8611
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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