Ethanol → HCID 178510426, compound

HRID 1508030Notes

Reaction equation

HRID 1508030 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]2[N:16](COCC[Si](C)(C)C)[CH:17]=[C:18]([C:20]#[N:21])[N:19]=2)=[O:14])=[C:8]([C:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]=2)[CH:7]=1)(=[O:3])[NH2:2].CCO.C(O)(C(F)(F)F)=O.C(O)CC>C(Cl)Cl>[C:1]([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]2[NH:16][CH:17]=[C:18]([C:20]#[N:21])[N:19]=2)=[O:14])=[C:8]([C:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]=2)[CH:7]=1)(=[O:3])[NH2:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 10311-PropanolHCID 6422Trifluoroacetic acidHCID 58994553HCID 58994553, compound

Product 1

HCID 178510426HCID 178510426, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-(2-carbamoyl-ethyl)-2-cyclohex-1-enyl-phenyl]-amide (as prepared in the previous step, 150 mg, 0.304 mmol) in 2 mL of DCM was added 60 μL of EtOH followed by 1 mL of TFA. The resulting solution was stirred at RT for 3 h. The reaction was treated with 20 mL of n-propanol and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (2-5% MeOH/DCM) to afford 86.1 mg (78%) of the title compound as a white solid. 1H-NMR (CD3OD; 400 MHz): δ 8.08 (d, 1H, J=8.3 Hz), 8.00 (s, 1H), 7.14 (dd, 1H, J=8.3, 2.2 Hz), 7.06 (d, 1H, J=2.2 Hz), 5.79 (m, 1H), 2.89 (t, 2H, J=7.7 Hz), 2.50 (t, 2H, J=7.7 Hz), 2.20-2.30 (m, 4H), 1.72-1.88 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C20H21N5O2, 364.2 (M+H). found 364.1.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash chromatography on silica gel (2-5% MeOH/DCM)

Sources & evidence

ORD record
ord-e6360de0b8cd4bcfb249b022435ef6ae
Source dataset
uspto-grants-2015_12
Patent number
US09221797B2

Reaction notes

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