Trifluoroacetic acid → HCID 178424543, compound

HRID 1711332Notes

Reaction equation

HRID 1711332 reaction equation
C([O:3][C:4](=[O:29])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[NH:15][CH:16]=[C:17]([C:19]#[N:20])[N:18]=2)=[O:13])=[C:7]([C:21]2[CH2:26][CH2:25][C:24]([CH3:28])([CH3:27])[CH2:23][CH:22]=2)[CH:6]=1)C.[OH-].[K+].C(O)(C(F)(F)F)=O>CCO>[C:19]([C:17]1[N:18]=[C:14]([C:12]([NH:11][C:8]2[CH:9]=[CH:10][C:5]([C:4]([OH:29])=[O:3])=[CH:6][C:7]=2[C:21]2[CH2:26][CH2:25][C:24]([CH3:28])([CH3:27])[CH2:23][CH:22]=2)=[O:13])[NH:15][CH:16]=1)#[N:20]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14797Potassium HydroxideHCID 178469042HCID 178469042, compound

Product 1

HCID 178424543HCID 178424543, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-[(4-cyano-1H-imidazole-2-carbonyl)-amino]-3-(4,4-dimethyl-cyclohex-1-enyl)-benzoic acid ethyl ester (50 mg, 0.13 mmol) in 1 mL of EtOH was added a 2 N aqueous solution of KOH (0.20 mL, 0.10 mmol) and the mixture heated to 60° C. for 6 h. The pH was adjusted to 2 with 2 N aq TFA and the title compound was purified by RP-HPLC eluting with a linear gradient of 30% to 50% acetonitrile in 0.1% TFA/H2O over 10 min on a C18 column giving 40 mg (87%) of a white solid. 1H-NMR (CD3OD, 400 MHz): δ 8.48 (d, J=8.6 Hz, 1H), 8.04 (s, 1H), 7.96 (dd, J=8.6, 2.0 Hz, 1H), 7.85 (d, J=2.0 Hz, 1H), 5.85 (m, 1H), 2.40-2.32 (m, 2H), 2.17-2.13 (m, 2H), 1.66 (t, J=6.3 Hz, 2H), 1.15 (s, 6H). Mass spectrum (APCI, m/z): Calcd. for C20H20N4O3, 363.2 (M-H), found 363.4.

Workup

  1. customthe title compound was purified by RP-HPLC
  2. washeluting with a linear gradient of 30% to 50% acetonitrile in 0.1% TFA/H2O over 10 min on a C18 column

Sources & evidence

ORD record
ord-6eae8085ceb040bc820cae063fa03902
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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