Trifluoroacetic acid → HCID 24875124, compound

HRID 1508105Notes

Reaction equation

HRID 1508105 reaction equation
C([O:3][C:4](=[O:31])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[NH:17][C:18]([C:21]#[N:22])=[CH:19][N:20]=2)=[O:15])=[C:9]([C:23]2[CH2:28][CH2:27][C:26]([CH3:30])([CH3:29])[CH2:25][CH:24]=2)[CH:8]=1)[OH:6])C.[OH-].[K+].C(O)(C(F)(F)F)=O>CCO>[C:21]([C:18]1[NH:17][C:16]([C:14]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([CH:5]([OH:6])[C:4]([OH:31])=[O:3])=[CH:8][C:9]=2[C:23]2[CH2:28][CH2:27][C:26]([CH3:30])([CH3:29])[CH2:25][CH:24]=2)=[O:15])=[N:20][CH:19]=1)#[N:22]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14797Potassium HydroxideHCID 58994583HCID 58994583, compound

Product 1

HCID 24875124HCID 24875124, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of [4-[(5-cyano-1H-imidazole-2-carbonyl)-amino]-3-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-hydroxy-acetic acid ethyl ester (as prepared in the previous step)(30.0 mg, 71 μmol) in 0.2 mL of EtOH at RT was added a 2N KOH solution (71 uL, 14.2 μmol) and the reaction stirred for 2 h. The pH was then adjusted to 2 with a 2 M TFA solution and the title compound was purified by RP-HPLC, eluting with a linear gradient of 20% to 50% CH3CN in 0.1% TFA/H2O over 10 min to give 20 mg (71%) of a white solid. 1H-NMR (400 MHz, CD3OD): δ 8.24 (d, J=8.4 Hz, 1H), 8.00 (s, 1H), 7.40 (dd, J=8.4, 2.1 Hz, 1H), 7.33 (d, J=2.1 Hz, 1H), 5.78 (m, 1H), 5.15 (s, 1H), 2.33 (m, 2H), 2.10 (m, 2H), 1.62 (t, J=6.3, 6.3 Hz, 2H), 1.11 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C21H22N4O2, 395.2 (M+H). found 395.1.

Workup

  1. customthe title compound was purified by RP-HPLC
  2. washeluting with a linear gradient of 20% to 50% CH3CN in 0.1% TFA/H2O over 10 min

Sources & evidence

ORD record
ord-65f1704584764f88a26584cea1d67bb1
Source dataset
uspto-grants-2015_12
Patent number
US09221797B2

Reaction notes

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