1-Propanol → HCID 178510431, compound

HRID 1711245Notes

Reaction equation

HRID 1711245 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[N:14](COCC[Si](C)(C)C)[CH:15]=[C:16]([C:18]#[N:19])[N:17]=2)=[O:12])=[C:6]([C:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]=2)[CH:5]=1)(=[O:3])[NH2:2].C(O)(C(F)(F)F)=O.C(O)CC>C(Cl)Cl>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[NH:14][CH:15]=[C:16]([C:18]#[N:19])[N:17]=2)=[O:12])=[C:6]([C:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]=2)[CH:5]=1)(=[O:3])[NH2:2]

Participants

5

Reactant 3

HCID 10311-PropanolHCID 6422Trifluoroacetic acidHCID 587548354-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (4-carbamoyl-2-cyclohex-1-enyl-phenyl)-amide

Product 1

HCID 178510431HCID 178510431, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (4-carbamoyl-2-cyclohex-1-enyl-phenyl)-amide (as prepared in the previous step, 200 mg, 0.430 mmol) in 6 mL of DCM was added 2 mL of TFA. After stirring at RT for 3 h, the mixture was treated with 20 mL of n-propanol and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (4-6% MeOH/DCM) to afford 88.0 mg (61%) of the title compound as a white solid. 1H-NMR (CD3OD; 400 MHz): δ 8.41 (d, 1H, J=8.6 Hz), 8.03 (s, 1H), 7.81 (dd, 1H, J=8.6, 2.3 Hz), 7.74 (d, 1H, J=2.3 Hz), 5.89 (m, 1H), 2.20-2.38 (m, 4H), 1.71-1.95 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C18H17N5O2, 336.1 (M+H), found 336.1.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash chromatography on silica gel (4-6% MeOH/DCM)

Sources & evidence

ORD record
ord-dddef2fead7348f598cd36770119d8d9
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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