Ethanol → HCID 178424571, compound

HRID 1711284Notes

Reaction equation

HRID 1711284 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[N:19](COCC[Si](C)(C)C)[CH:20]=[C:21]([C:23]#[N:24])[N:22]=2)=[O:17])=[C:11]([C:33]2[CH2:38][CH2:37][C:36]([CH3:40])([CH3:39])[CH2:35][CH:34]=2)[CH:10]=1)(=[O:8])=[O:7])(C)(C)C.CCO.C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:39][C:36]1([CH3:40])[CH2:37][CH2:38][C:33]([C:11]2[CH:10]=[C:9]([S:6](=[O:7])(=[O:8])[NH2:5])[CH:14]=[CH:13][C:12]=2[NH:15][C:16]([C:18]2[NH:19][CH:20]=[C:21]([C:23]#[N:24])[N:22]=2)=[O:17])=[CH:34][CH2:35]1

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 587548314-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-tert-butylsulfamoyl-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide

Product 1

HCID 178424571HCID 178424571, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 100 mg (0.171 mmol) of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-tert-butylsulfamoyl-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide (as prepared in the previous step) in CH2Cl2 (10 mL) was treated with 62.0 μL EtOH, 67.0 μL (0.616 mmol) of anisole, and TFA (750 μL) at RT for 18 h. EtOH (3 mL) was added, the mixture was concentrated, the residue was subjected again to the conditions above except that 900 μL of TFA was used, and then was subjected a third time with 1.70 mL of TFA. Solvents were evaporated in vacuo. Purification of the residue by RP-HPLC (C18) with 20-100% CH3CN in 0.1% TFA/H2O over 30 min afforded 27.7 mg (41%) of the title compound as a white solid: 1H-NMR (CD3OD; 400 MHz): δ 8.40 (d, 1H, J=8.8 Hz), 7.92 (s, 1H), 7.71 (dd, 1H, J=8.8, 2.4 Hz), 7.62 (d, 1H, J=2.4 Hz), 5.80-5.73 (m, 1H), 2.30-2.21 (m, 2H), 2.08-1.99 (m, 2H), 1.60-1.50 (m, 2H), 1.02 (s, 6H).

Workup

  1. concentrationthe mixture was concentrated
  2. customSolvents were evaporated in vacuo
  3. customPurification of the residue by RP-HPLC (C18) with 20-100% CH3CN in 0.1% TFA/H2O over 30 min

Sources & evidence

ORD record
ord-1658622a270749baa45a5ac4ecb604ed
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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