Ethanol → HCID 178510427, compound

HRID 1508108Notes

Reaction equation

HRID 1508108 reaction equation
C([O:5][C:6](=[O:39])[CH:7]=[CH:8][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][CH2:36][CH2:35][CH:34]=2)[CH:10]=1)(C)(C)C.C(O)(C(F)(F)F)=O.CCO>C(Cl)Cl>[C:23]([C:21]1[N:22]=[C:18]([C:16]([NH:15][C:12]2[CH:13]=[CH:14][C:9]([CH:8]=[CH:7][C:6]([OH:39])=[O:5])=[CH:10][C:11]=2[C:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]=2)=[O:17])[NH:19][CH:20]=1)#[N:24]

Participants

5

Reactant 3

HCID 702EthanolHCID 6422Trifluoroacetic acidHCID 69007915HCID 69007915, compound

Product 1

HCID 178510427HCID 178510427, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-{[4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbonyl]-amino}-3-cyclohex-1-enyl-phenyl)-acrylic acid tert-butyl ester (30 mg, 0.055 mmol)(as prepared in the previous step) in 1.0 mL of DCM was added 0.30 mL of TFA, 0.026 mL of EtOH and stirred at RT for 2 h. The mixture was concentrated and the residue triturated with MeOH to give 19 mg (95%) of the title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6): δ 14.39 (br s, 1H), 9.83 (s, 1H), 8.38 (d, J=2.5 Hz, 1H), 8.15 (d, J=8.5 Hz, 1H), 7.65 (dd, J=8.5, 1.9 Hz, 1H), 7.57 (d, J=1.9 Hz, 1H), 7.56 (d, J=16.0 Hz, 1H), 6.53 (d, J=16.0 Hz, 1H), 5.83 (m, 1H), 2.31-2.14 (m, 4H), 1.81-1.65 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C20H18N4O3, 363.1 (M+H). found 363.0.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue triturated with MeOH

Sources & evidence

ORD record
ord-2825c1c0b19045099d2fd49cad1597bd
Source dataset
uspto-grants-2015_12
Patent number
US09221797B2

Reaction notes

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