Methanol → HCID 178424459, compound

HRID 447966Notes

Reaction equation

HRID 447966 reaction equation
[CH3:1][C:2]1([CH3:40])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([CH:14]3[CH2:19][C:18](=[O:20])[NH:17][C:16](=[O:21])[CH2:15]3)[CH:11]=[CH:10][C:9]=2[NH:22][C:23]([C:25]2[N:26](COCC[Si](C)(C)C)[CH:27]=[C:28]([C:30]#[N:31])[N:29]=2)=[O:24])=[CH:4][CH2:3]1.CO.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]1([CH3:40])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([CH:14]3[CH2:15][C:16](=[O:21])[NH:17][C:18](=[O:20])[CH2:19]3)[CH:11]=[CH:10][C:9]=2[NH:22][C:23]([C:25]2[NH:26][CH:27]=[C:28]([C:30]#[N:31])[N:29]=2)=[O:24])=[CH:4][CH2:3]1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 6422Trifluoroacetic acidHCID 597712624-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-(4,4-dimethyl-cyclohex-1-enyl)-4-(2,6-dioxo-piperidin-4-yl)-phenyl]-amide

Product 1

HCID 178424459HCID 178424459, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 190 mg (0.338 mmol) of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-(4,4-dimethyl-cyclohex-1-enyl)-4-(2,6-dioxo-piperidin-4-yl)-phenyl]-amide (as prepared in the previous step) in CH2Cl2 (10 mL) was treated with MeOH (200 μL) and TFA (3 mL) at RT for 1.5 h. MeOH (30 mL) was added, the mixture was concentrated to half volume, MeOH (15 mL) was added, and the solvents were removed completely in vacuo at <35° C. Silica gel chromatography of the residue with 25-75% EtOAc-hexane afforded 92.9 mg (64%) of the title compound as a white solid: 1H-NMR (CD3OD; 400 MHz): δ 8.22 (d, 1H, J=8.4 Hz), 8.02 (s, 1H), 7.26 (dd, 1H, J=8.4, 2.4 Hz), 7.18 (d, 1H, J=2.4 Hz), 5.79-5.75 (m, 1H), 3.52-3.42 (m, 1H), 2.93-2.76 (m, 4H), 2.37-2.30 (m, 2H), 2.12-2.07 (m, 2H), 1.62 (t, 2H, J=5.6 Hz), 1.10 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C24H25N5O3, 432.2 (M+H), found 432.1.

Workup

  1. concentrationthe mixture was concentrated to half volume, MeOH (15 mL)
  2. additionwas added
  3. customthe solvents were removed completely in vacuo at <35° C

Sources & evidence

ORD record
ord-ffea6e48e18849c598a9996b2c593a17
Source dataset
uspto-grants-2013_07
Patent number
US08481564B2

Reaction notes

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