Hydrochloric Acid → HCID 42605949, compound

HRID 1255446Notes

Reaction equation

Cl.Cl[C:3]1[N:12]=[CH:11][C:10]2[N:9]([CH3:13])[C:8](=[O:14])[C@@H:7]([CH2:15][CH3:16])[N:6]([C@@H:17]3[CH2:21][CH2:20][C:19]([F:23])([F:22])[CH2:18]3)[C:5]=2[N:4]=1.[NH2:24][C:25]1[CH:35]=[CH:34][C:28]([C:29]([NH:31][CH2:32][CH3:33])=[O:30])=[CH:27][C:26]=1[O:36][CH3:37]>C(O)C.O>[F:22][C:19]1([F:23])[CH2:20][CH2:21][C@@H:17]([N:6]2[C:5]3[N:4]=[C:3]([NH:24][C:25]4[CH:35]=[CH:34][C:28]([C:29]([NH:31][CH2:32][CH3:33])=[O:30])=[CH:27][C:26]=4[O:36][CH3:37])[N:12]=[CH:11][C:10]=3[N:9]([CH3:13])[C:8](=[O:14])[C@H:7]2[CH2:15][CH3:16])[CH2:18]1

Participants

Conditions

Temperature: 95 °C

Procedure

Concentrated hydrochloric acid (42 μl) was added to a mixture of (R)-2-chloro-8-((R)-3,3-difluorocyclopentyl)-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one (80 mg, 0.24 mmol) and 4-amino-N-ethyl-3-methoxybenzamide (70.47 mg, 0.36 mmol) in ethanol (1.2 mL) and water (4.8 mL). The reaction mixture was heated to 95° C. and stirred for 18 hours. The reaction mixture was concentrated in vacuo. The residue was taken up with dichloromethane, washed with an aqueous saturated solution of sodium bicarbonate and brine. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography to afford the desired compound as a white solid (89 mg, 75% yield).

Workup

concentrationThe reaction mixture was concentrated in vacuo
washwashed with an aqueous saturated solution of sodium bicarbonate and brine
dry with materialThe organic layer was dried over magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was purified on silica gel by flash column chromatography

Sources & evidence

ORD record: ord-fd6e9390367140bdbfe3fbdedcd72740
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461149B2

Reaction notes

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