Ethanol → HCID 178510418, compound

HRID 447973Notes

Reaction equation

HRID 447973 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([CH:13]3[CH2:18][NH:17][C:16](=[O:19])[NH:15][CH2:14]3)[CH:10]=[CH:9][C:8]=2[NH:20][C:21]([C:23]2[N:24](COCC[Si](C)(C)C)[CH:25]=[C:26]([C:28]#[N:29])[N:27]=2)=[O:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.CCO.[C:41]([OH:47])([C:43]([F:46])([F:45])[F:44])=[O:42]>C(Cl)Cl>[F:44][C:43]([F:46])([F:45])[C:41]([OH:47])=[O:42].[C:1]1([C:7]2[CH:12]=[C:11]([CH:13]3[CH2:18][NH:17][C:16](=[O:19])[NH:15][CH2:14]3)[CH:10]=[CH:9][C:8]=2[NH:20][C:21]([C:23]2[NH:24][CH:25]=[C:26]([C:28]#[N:29])[N:27]=2)=[O:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6422Trifluoroacetic acidHCID 597711634-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(2-oxo-hexahydro-pyrimidin-5-yl)-phenyl]-amide

Product 1

HCID 178510418HCID 178510418, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(2-oxo-hexahydro-pyrimidin-5-yl)-phenyl]-amide (as prepared in the previous step, 14 mg, 0.026 mmol) was dissolved in DCM (1 mL), EtOH (30 μL) and TFA (0.3 mL). The resulting mixture was stirred overnight and concentrated. The residue obtained was subjected to RP-HPLC eluting with 20% to 100% CH3CN in 0.1% TFA/H2O over 20 min on a C18 column to obtain the title compound (1.1 mg, 8%): 1H-NMR (CD3OD/CDCl3; 400 MHz): δ 8.23 (d, 1H, J=8.0 Hz), 7.90 (s, 1H), 7.20 (dd, 1H, J=8.0, 2.2 Hz), 7.09 (d, 1H, J=2.2 Hz), 5.75 (br s, 1H), 3.47 (4H, m), 3.17 (m, 1H), 2.22-2.33 (m, 4H), 1.72-1.83 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C21H22N6O2, 391.3 (M+H), found 391.2.

Workup

  1. concentrationconcentrated
  2. customThe residue obtained
  3. washeluting with 20% to 100% CH3CN in 0.1% TFA/H2O over 20 min on a C18 column

Sources & evidence

ORD record
ord-9a0b472038134dfd9134c337de0dbf8a
Source dataset
uspto-grants-2013_07
Patent number
US08481564B2

Reaction notes

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