Hydrochloric Acid → HCID 66628232, compound

HRID 1046848Notes

Reaction equation

HRID 1046848 reaction equation
[OH-].[Li+].C([O:6][CH2:7][C:8]([NH:10][C:11]1[N:40]=[C:14]2[N:15]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=3)[C:16]([CH3:29])=[C:17]([C:27]#[N:28])[C@@H:18]([C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=3)[N:13]2[N:12]=1)=[O:9])(=O)C.Cl>O.C1COCC1>[C:27]([C:17]1[C@@H:18]([C:19]2[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=2)[N:13]2[N:12]=[C:11]([NH:10][C:8](=[O:9])[CH2:7][OH:6])[N:40]=[C:14]2[N:15]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:38])([F:39])[F:37])[CH:31]=2)[C:16]=1[CH3:29])#[N:28]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66628223HCID 66628223, compound

Product 1

HCID 66628232HCID 66628232, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

At RT, a solution of lithium hydroxide (2.3 mg, 95.9 μmol, 5 eq.) in water (125 μl) was added to a solution of 2-((7R)-6-cyano-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-2-ylamino)-2-oxoethyl acetate (10.0 mg, 19.2 μmol; Example 31) in THF (625 μl). After 1 h of stirring, conversion was found to be complete. 1 N hydrochloric acid (153 μl, 8 eq.) was added, and the reaction mixture was directly purified by preparative HPLC (Kromasil C18 column, 5 μm, 50×20 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (6.5 mg, 71% of theory).

Workup

  1. customthe reaction mixture was directly purified by preparative HPLC (Kromasil C18 column, 5 μm, 50×20 mm; mobile phase: acetonitrile-water-0.1% TFA)
  2. customAfter lyophilization, the product was obtained as a solid (6.5 mg, 71% of theory)

Sources & evidence

ORD record
ord-445feaca9f9a433f9046e09bb5b1026e
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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