Methanol → HCID 178510434, compound

HRID 1711277Notes

Reaction equation

HRID 1711277 reaction equation
[C:1]1([C:7]2[C:12]([NH:13][C:14]([C:16]3[N:17](COCC[Si](C)(C)C)[CH:18]=[C:19]([C:21]#[N:22])[N:20]=3)=[O:15])=[CH:11][CH:10]=[CH:9][N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.CO.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]>C(Cl)Cl>[F:36][C:35]([F:38])([F:37])[C:33]([OH:39])=[O:34].[C:1]1([C:7]2[C:12]([NH:13][C:14]([C:16]3[NH:17][CH:18]=[C:19]([C:21]#[N:22])[N:20]=3)=[O:15])=[CH:11][CH:10]=[CH:9][N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 6422Trifluoroacetic acidHCID 587548614-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (2-cyclohex-1-enyl-pyridin-3-yl)-amide

Product 1

HCID 178510434HCID 178510434, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 615 mg (1.45 mmol) of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (2-cyclohex-1-enyl-pyridin-3-yl)-amide (as prepared in the previous step) in CH2Cl2 (12 mL) was treated with MeOH (100 μL) and TFA (3 mL) at RT for 3.5 h. MeOH (5 mL) was added to the mixture before concentrating in vacuo. RP-HPLC (C18) of the residue with 10-80% CH3CN in 0.1% TFA/H2O over 30 min afforded 177 mg (30%) of the title compound as a white solid: 1H-NMR (CD3OD; 400 MHz): δ 9.03 (dd, 1H, J=8.4, 1.6 Hz), 8.45 (dd, 1H, J=5.2, 1.6 Hz), 8.07 (s, 1H), 7.81-7.74 (m, 1H), 6.36-6.29 (m, 1H), 2.49-2.34 (m, 4H), 1.97-1.79 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C16H15N5O, 294.1 (M+H), found 294.1.

Workup

  1. concentrationbefore concentrating in vacuo

Sources & evidence

ORD record
ord-6dd0281ef63e43faa52fcf8c5039a812
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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