Ammonium Acetate → Dimethyl[6-(1-aminoethyl)-4-chloro-3'-fluoro-3-methylbiphenyl-2-yl]imidodicarbonate

HRID 510849Notes

Reaction equation

[C:1]([C:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)=[C:8]([N:17]([C:22]([O:24][CH3:25])=[O:23])[C:18]([O:20][CH3:21])=[O:19])[C:7]([CH3:26])=[C:6]([Cl:27])[CH:5]=1)(=O)[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:34].[Na+]>CO.C(#N)C>[NH2:34][CH:1]([C:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)=[C:8]([N:17]([C:22]([O:24][CH3:25])=[O:23])[C:18]([O:20][CH3:21])=[O:19])[C:7]([CH3:26])=[C:6]([Cl:27])[CH:5]=1)[CH3:2]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of dimethyl (6-acetyl-4-chloro-3′-fluoro-3-methylbiphenyl-2-yl)imidodicarbonate (67 mg, 0.17 mmol), ammonium acetate (131 mg, 1.70 mmol) and sodium cyanoborohydride (21 mg, 0.34 mmol) in methanol (0.6 mL) and acetonitrile (0.6 mL) was heated at 65° C. overnight in a sealed tube. The mixture was then cooled to room temperature and quenched with saturated sodium bicarbonate and extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and evaporated to dryness. The crude product was used directly in next step (67 mg, 100%). LCMS calculated for C19H21ClFN2O4 (M+H)+: m/z=395.1. found: 395.1.

Workup

temperatureThe mixture was then cooled to room temperature
customquenched with saturated sodium bicarbonate
extractionextracted with dichloromethane
dry with materialThe combined extracts were dried over magnesium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-000e9c4f2cd145f9b03e0f9f93a57e76
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096600B2

Reaction notes

Loading…