Trifluoroacetic acid → HCID 178424657, compound

HRID 1711273Notes

Reaction equation

HRID 1711273 reaction equation
[CH3:1][C:2]1([CH3:32])[CH2:7][CH2:6][C:5]([C:8]2[C:13]([NH:14][C:15]([C:17]3[N:18](COCC[Si](C)(C)C)[CH:19]=[C:20]([C:22]#[N:23])[N:21]=3)=[O:16])=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH2:3]1.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]>C(Cl)Cl.CO>[F:36][C:35]([F:38])([F:37])[C:33]([OH:39])=[O:34].[CH3:1][C:2]1([CH3:32])[CH2:7][CH2:6][C:5]([C:8]2[C:13]([NH:14][C:15]([C:17]3[NH:18][CH:19]=[C:20]([C:22]#[N:23])[N:21]=3)=[O:16])=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH2:3]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 587548574-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-(4,4-dimethyl-cyclohex-1-enyl)-pyridin-3-yl]-amide

Product 1

HCID 178424657HCID 178424657, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 95.0 mg (0.210 mmol) of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-(4,4-dimethyl-cyclohex-1-enyl)-pyridin-3-yl]-amide (as prepared in the previous step) in CH2Cl2 (15 mL) was treated with MeOH (1 drop) and TFA (1 mL). The mixture was stirred at RT for 2 days, and the solvents were evaporated in vacuo. Silica gel chromatography of the residue on a 20-g Isolute SPE column with 25% EtOAc-hexane and RP-HPLC (C18) with 10-80% CH3CN in 0.1% TFA/H2O over 30 min afforded 36.0 mg (39%) of the title compound as a white solid: 1H-NMR (CD3OD; 400 MHz): δ 9.02 (dd, 1H, J=8.4, 1.6 Hz), 8.44 (dd, 1H, J=5.2, 1.6 Hz), 8.06 (s, 1H), 7.76-7.71 (m, 1H), 6.22 (sept, 1H, J=2.0 Hz), 2.50-2.43 (m, 2H), 2.18-2.13 (m, 2H), 1.65 (t, 2H, J=6.4 Hz), 1.11 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C18H19N5O, 322.1 (M+H), found 322.1.

Workup

  1. customthe solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-754a56f232814db3998ce2731c0e7add
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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