Sodium hydride → 1-(2-{(1S,2R)-2-[1-(2,2-Dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]cyclopropyl}ethyl)-3-methylimidazolidine-2,4-dione

HRID 629913Notes

Reaction equation

[CH3:1][C:2]([CH3:25])([CH3:24])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C@@H:13]3[CH2:15][C@H:14]3[CH2:16][CH2:17]S(C)(=O)=O)=[CH:10][CH:11]=2)[N:6]([CH3:22])[C:5]1=[O:23].[CH3:26][N:27]1[C:31](=[O:32])[CH2:30][NH:29][C:28]1=[O:33].[H-].[Na+]>CN(C=O)C>[CH3:1][C:2]([CH3:25])([CH3:24])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C@@H:13]3[CH2:15][C@H:14]3[CH2:16][CH2:17][N:29]3[CH2:30][C:31](=[O:32])[N:27]([CH3:26])[C:28]3=[O:33])=[CH:10][CH:11]=2)[N:6]([CH3:22])[C:5]1=[O:23]

Participants

Conditions

Temperature: 0 °C

Procedure

1-(2,2-Dimethylpropyl)-3-methyl-5-{(1R,2S)-2-[2-(methylsulfonyl)ethyl]-cyclopropyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (32-5, 39 mg, 0.10 mmol, 1.0 equiv) was added to anhydrous DMF (0.50 mL) and cooled to 0° C. 3-Methylimidazolidine-2,4-dione (31-6, 58 mg, 0.51 mmol, 5.0 equiv) and NaH (20 mg, 0.51 mmol, 5.0 equiv, 60% dispersion in oil) were added sequentially and the resulting mixture was warmed to RT. After 18 h, LCMS showed complete consumption of 32-5. Purification by reverse-phase HPLC (10-100% 0.1% TFA in H2O:CH3CN) afforded 32-6 as a colorless oil. MS m/z (M+H): calculated=400.2343; observed=400.2342.

Workup

temperaturethe resulting mixture was warmed to RT
customconsumption of 32-5
customPurification by reverse-phase HPLC (10-100% 0.1% TFA in H2O:CH3CN)

Sources & evidence

ORD record: ord-80ef589b16d1412e807a75247afbdf79
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315518B2

Reaction notes

Loading…