4-{6-amino-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-3-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester → 7-[(R)-1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-3-(1,2,3,6-tetrahydropyridin-4-yl)furo[3,2-c]pyridin-6-ylamine

HRID 911956Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:18]3[CH:19]=[N:20][C:21]([NH2:35])=[C:22]([O:23][C@@H:24]([C:26]4[C:31]([Cl:32])=[CH:30][CH:29]=[C:28]([F:33])[C:27]=4[Cl:34])[CH3:25])[C:17]=3[O:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[Cl:34][C:27]1[C:28]([F:33])=[CH:29][CH:30]=[C:31]([Cl:32])[C:26]=1[C@H:24]([O:23][C:22]1[C:17]2[O:16][CH:15]=[C:14]([C:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=3)[C:18]=2[CH:19]=[N:20][C:21]=1[NH2:35])[CH3:25]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 4-{6-amino-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-3-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (98.0 mg, 0.188 mmol) in 4 M HCl in 1,4-dioxane (8 mL) was cooled to 0° C., then stirred at 50° C. for 2 h. The material was concentrated in vacuo and then extracted with DCM and sat. aq. NaHCO3. The organic layer was concentrated in vacuo to afford the title compound as a brown solid. 1H NMR (CDCl3, 400 MHz): δ=1.86 (d, J=6.8 Hz, 3H), 2.37-2.47 (m, 2H), 3.15 (t, J=5.8 Hz, 2H), 3.60 (d, J=2.8 Hz, 2H), 4.74 (s, 2H), 6.28 (br, s, 1H), 6.52 (q, J=6.7 Hz, 1H), 7.02-7.08 (m, 1H), 7.27-7.32 (m, 1H), 7.37 (s, 1H), 8.25 (s, 1H). MS (ES+): m/z 422.06 [MH+]. HPLC: tR=2.23 min (ZQ3, polar—5 min).

Workup

concentrationThe material was concentrated in vacuo
extractionextracted with DCM and sat. aq. NaHCO3
concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record: ord-b3751a34aa9f43bbba2fcba25ded68ab
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022206B2

Reaction notes

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