Ammonium Acetate → 1-{5-chloro-8-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]quinolin-7-yl]ethanamine

HRID 1192505Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=O)[CH3:13])[C:9]([N:15]2[CH2:19][CH2:18][CH2:17][C@@H:16]2[CH2:20][O:21][CH3:22])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C([O-])(=O)C.[NH4+].C([BH3-])#[N:29].[Na+]>CO.C(#N)C>[Cl:1][C:2]1[CH:11]=[C:10]([CH:12]([NH2:29])[CH3:13])[C:9]([N:15]2[CH2:19][CH2:18][CH2:17][C@@H:16]2[CH2:20][O:21][CH3:22])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 1-{5-chloro-8-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]quinolin-7-yl}ethanone (14 mg, 0.044 mmol) and ammonium acetate (33.8 mg, 0.439 mmol) in methanol (0.25 mL,) and acetonitrile (0.25 mL) was heated at 65° C. in a sealed tube for 30 minutes. After cooling, sodium cyanoborohydride (5.52 mg, 0.0878 mmol) was added to the resultant mixture. The reaction was heated at 65° C. for another 4 hours, then cooled to room temperature, quenched with saturated sodium bicarbonate, and extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and evaporated to dryness. The residue was used directly in the next step. LCMS calculated for C17H23ClN3O(M+H)+: m/z=320.2; found: 302.1.

Workup

temperatureAfter cooling
temperatureThe reaction was heated at 65° C. for another 4 hours
temperaturecooled 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-914418fe539644998c2fc5e55ff4bd5f
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680108B2

Reaction notes

Loading…