Ethyl Bromide → 5-[1-(1-Ethyl-4-piperidyl)pyrazol-4-yl]-3-oxazolo[4,5-b]pyridin-2-yl-pyridin-2-amine

HRID 908462Notes

Reaction equation

Br[CH2:2][CH3:3].[O:4]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]1[C:13]1[C:14]([NH2:30])=[N:15][CH:16]=[C:17]([C:19]2[CH:20]=[N:21][N:22]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[CH:23]=2)[CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:2]([N:27]1[CH2:26][CH2:25][CH:24]([N:22]2[CH:23]=[C:19]([C:17]3[CH:18]=[C:13]([C:5]4[O:4][C:12]5[C:7]([N:6]=4)=[N:8][CH:9]=[CH:10][CH:11]=5)[C:14]([NH2:30])=[N:15][CH:16]=3)[CH:20]=[N:21]2)[CH2:29][CH2:28]1)[CH3:3]

Participants

Conditions

Temperature: 25 °C

Procedure

Bromoethane (0.019 ml) at 0° C. was added to a stirred mixture of 3-oxazolo[4,5-b]pyridin-2-yl-5-[1-(4-piperidyl)pyrazol-4-yl]pyridin-2-amine (90 mg) and potassium carbonate (68.8 mg) and DMF (1.5 mL) over a period of 5 minutes under argon. The resulting suspension was stirred at 25° C. for 20 hours. The solvent was evaporated. A solution of ammonia in methanol 7N (1 ml) was added and the mixture was adsorbed on silica gel. The crude product was purified by flash chromatography on silica gel eluting with 1 to 5% methanolic ammonia (7 N) in dichloromethane. The solvent was evaporated to dryness to afford 5-[1-(1-ethyl-4-piperidyl)pyrazol-4-yl]-3-oxazolo[4,5-b]pyridin-2-yl-pyridin-2-amine (60.0 mg) as a solid. NMR Spectrum: (DMSOd6) 1.03 (t, 3H), 1.91-2.10 (m, 6H), 2.38 (q, 2H), 2.94-3.01 (m, 2H), 4.09-4.18 (m, 1H), 7.48 (dd, 1H), 7.67 (bs, 2H), 7.92 (s, 1H), 8.23 (dd, 1H), 8.34 (s, 1H), 8.46 (d, 1H), 8.55 (dd, 1H), 8.58 (d, 1H); Mass spectrum: M+H+ 390.

Workup

customThe solvent was evaporated
additionA solution of ammonia in methanol 7N (1 ml) was added
customThe crude product was purified by flash chromatography on silica gel eluting with 1 to 5% methanolic ammonia (7 N) in dichloromethane
customThe solvent was evaporated to dryness

Sources & evidence

ORD record: ord-12b0f836cf9d4ebdb71956056007ec41
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017611B2

Reaction notes

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