Hydrochloric Acid → HCID 58032638, compound

HRID 2200978Notes

Reaction equation

HRID 2200978 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[N:44]=[C:15]2[N:16]([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:43])([F:42])[F:41])[CH:35]=3)[C:17]([CH3:33])=[C:18]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:19]([C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=3)[N:14]2[N:13]=1)=[O:10])[C:2]1C=CC=CC=1.[OH-].[Li+].Cl>C1COCC1.O.C(O)C>[C:26]([C:23]1[CH:24]=[CH:25][C:20]([CH:19]2[N:14]3[N:13]=[C:12]([NH:11][C:9]([O:8][CH2:1][CH3:2])=[O:10])[N:44]=[C:15]3[N:16]([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:41])([F:43])[F:42])[CH:35]=3)[C:17]([CH3:33])=[C:18]2[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:21][CH:22]=1)#[N:27]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58032592HCID 58032592, compound

Product 1

HCID 58032638HCID 58032638, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under an atmosphere of argon protective gas, ethyl 2-[(benzyloxy)carbonyl]amino-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate (125 mg, 207 μmol) was dissolved in a mixture of THF (0.9 ml), water (0.6 ml) and ethanol (3.8 ml). After addition of solid lithium hydroxide (14.9 mg, 620 μmol, 3 eq.), the reaction mixture was heated at 55 C for 1.5 h. In an ice-bath, the mixture was acidified with 1 N hydrochloric acid (4.1 ml) and then purified by preparative HPLC (Kromasil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (4.8 mg, 5% of theory).

Workup

  1. temperaturethe reaction mixture was heated at 55 C for 1.5 h
  2. custompurified by preparative HPLC (Kromasil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA)
  3. customAfter lyophilization, the product was obtained as a solid (4.8 mg, 5% of theory)

Sources & evidence

ORD record
ord-9cb8094df00142c896deb28431dbcde5
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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