Diisopropylethylamine → HCID 58398047, compound

HRID 451541Notes

Reaction equation

Cl.Cl.[F:3][C:4]1[CH:5]=[C:6]([C:11]2[C:12]3[N:13]([N:17]=[C:18]([NH:20][C@@H:21]4[CH2:26][CH2:25][NH:24][CH2:23][C@@H:22]4[O:27][CH3:28])[N:19]=3)[CH:14]=[CH:15][CH:16]=2)[CH:7]=[CH:8][C:9]=1[F:10].Cl[C:30]1[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32][N:31]=1.CCN(C(C)C)C(C)C>ClCCl.O1CCOCC1>[F:3][C:4]1[CH:5]=[C:6]([C:11]2[C:12]3[N:13]([N:17]=[C:18]([NH:20][C@@H:21]4[CH2:26][CH2:25][N:24]([C:30]5[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32][N:31]=5)[CH2:23][C@@H:22]4[O:27][CH3:28])[N:19]=3)[CH:14]=[CH:15][CH:16]=2)[CH:7]=[CH:8][C:9]=1[F:10]

Participants

Conditions

Temperature: 130 °C

Procedure

8-(3,4-Difluorophenyl)-N-((3S,4R)-3-methoxypiperidin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine dihydrochloride (28 mg, 64.8 μmol) was extracted with dichloromethane/2 M NaOH. The organic layers were washed with brine, dried over sodium sulfate and evaporated. The residue was dissolved in dioxane (0.5 mL) and to this solution 4-chloro-6-methylpyrimidine (9.2 mg, 71.2 μmol) and DIPEA (17.0 μL, 97.2 μmol) were added. Argon was bubbled through the solution for 5 minutes, and then heated in the microwave at 130° C. for 2×30 minutes. After evaporation, purification by chromatography (silica gel, 10 g, 0 to 10% methanol in dichloromethane) afforded the title compound (18 mg, 62%) as an off white foam.

Workup

washThe organic layers were washed with brine
dry with materialdried over sodium sulfate
customevaporated
additionwere added
customArgon was bubbled through the solution for 5 minutes
customAfter evaporation, purification by chromatography (silica gel, 10 g, 0 to 10% methanol in dichloromethane)

Sources & evidence

ORD record: ord-f168c428cbd844cbbb97716c93f1a69e
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486967B2

Reaction notes

Loading…