Ethanol → HCID 178510429, compound

HRID 1711292Notes

Reaction equation

HRID 1711292 reaction equation
C([NH:5][S:6]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]2[N:21](COCC[Si](C)(C)C)[CH:22]=[C:23]([C:25]#[N:26])[N:24]=2)=[O:19])=[C:13]([C:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH:36]=2)[CH:12]=1)(=[O:8])=[O:7])(C)(C)C.CCO.C1(OC)C=CC=CC=1.[C:52]([OH:58])([C:54]([F:57])([F:56])[F:55])=[O:53]>C(Cl)Cl>[F:55][C:54]([F:57])([F:56])[C:52]([OH:58])=[O:53].[C:35]1([C:13]2[CH:12]=[C:11]([CH2:10][CH2:9][S:6](=[O:7])(=[O:8])[NH2:5])[CH:16]=[CH:15][C:14]=2[NH:17][C:18]([C:20]2[NH:21][CH:22]=[C:23]([C:25]#[N:26])[N:24]=2)=[O:19])[CH2:40][CH2:39][CH2:38][CH2:37][CH:36]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6422Trifluoroacetic acid2×HCID 7519AnisoleHCID 587548884-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-(2-tert-butylsulfamoyl-ethyl)-2-cyclohex-1-enyl-phenyl]-amide

Product 1

HCID 178510429HCID 178510429, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-(2-tert-butylsulfamoyl-ethyl)-2-cyclohex-1-enyl-phenyl]-amide (as the prepared in previous step, 275 mg, 0.470 mmol) in DCM (5 mL), EtOH (140 μL), anisole (51 μL) and TFA (1.5 mL) were added. The resulting solution was stirred at RT for 6 h. An additional 0.35 mL of TFA was added and the resulting mixture was stirred at RT overnight. The reaction mixture was concentrated and the residue was subjected to RP-HPLC eluting with 20% to 100% CH3CN in 0.1% TFA/H2O over 20 min on a C18 column to afford the title compound (26.6 mg, 11%). 1H-NMR (DMSO-d6; 400 MHz): δ 9.72 (s, 1H), 8.31 (s, 1H), 7.85 (d, 1H, J=8.4 Hz), 7.17 (d, 1H, J=8.4 Hz), 7.10 (s, 1H), 6.82 (s, 2H), 5.72 (br s, 1H), 3.23 (m, 2H), 2.92 (m, 2H), 2.1-2.29 (m, 4H), 1.62-1.75 (m, 4H); Mass spectrum (ESI, m/z): Calcd. for C19H21N5O3S, 400.1 (M+H), found 400.1.

Workup

  1. stirringthe resulting mixture was stirred at RT overnight
  2. concentrationThe reaction mixture was concentrated
  3. washeluting with 20% to 100% CH3CN in 0.1% TFA/H2O over 20 min on a C18 column

Sources & evidence

ORD record
ord-aec39bb9bd474e2baa35cabf67d5363f
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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