HCID 57812510, compound → HCID 57812718, compound

HRID 911996Notes

Reaction equation

C[O:2][C:3]([C:5]1[C:9]2[CH:10]=[N:11][C:12]([NH2:26])=[C:13]([O:14][C@@H:15]([C:17]3[C:22]([Cl:23])=[CH:21][CH:20]=[C:19]([F:24])[C:18]=3[Cl:25])[CH3:16])[C:8]=2[O:7][CH:6]=1)=[O:4]>Cl>[NH2:26][C:12]1[N:11]=[CH:10][C:9]2[C:5]([C:3]([OH:4])=[O:2])=[CH:6][O:7][C:8]=2[C:13]=1[O:14][C@@H:15]([C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[C:19]([F:24])[C:18]=1[Cl:25])[CH3:16]

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 6-amino-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridine-3-carboxylic acid methyl ester (140 mg, 0.35 mmol) in 1N aq. HCl (5 mL) was heated at 100° C. for 7 h. The mixture was cooled to rt, and the off-white solid was collected by filtration to give the title compound. LC-MS (ES+): 384.96/386.96 [MH+]. 1H NMR (CD3OD, 400 MHz): δ 1.95 (d, J=6.6 Hz, 3H), 6.70 (q, J=6.6 Hz, 1H), 7.26 (m, 1H), 7.44 (dd, J=9.1, 4.8 Hz, 1H), 8.20 (s, 1H), 8.43 (s, 1H).

Workup

temperatureThe mixture was cooled to rt
filtrationthe off-white solid was collected by filtration

Sources & evidence

ORD record: ord-40355e5e08e446f996671bfebca17282
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022206B2

Reaction notes

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