HCID 54689915, compound → HCID 54689860, compound

HRID 1244131Notes

Reaction equation

C([O:8][C:9]1[C:14]([Cl:15])=[CH:13][C:12]([C:16]2[C:24]3[C:23]([OH:25])=[C:22]([C:26]#[N:27])[C:21](=[O:28])[NH:20][C:19]=3[S:18][CH:17]=2)=[CH:11][C:10]=1[Cl:29])C1C=CC=CC=1>Br.CC(O)=O>[Cl:29][C:10]1[CH:11]=[C:12]([C:16]2[C:24]3[C:23]([OH:25])=[C:22]([C:26]#[N:27])[C:21](=[O:28])[NH:20][C:19]=3[S:18][CH:17]=2)[CH:13]=[C:14]([Cl:15])[C:9]=1[OH:8]

Participants

Conditions

Temperature: 70 °C

Procedure

The 3-(4-benzyloxy-3,5-dichloro-phenyl)-4-hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile (125 mg, 0.281 mmol) was dissolved in 30% HBr/AcOH (1.3 mL) and sealed in a reaction tube with stirring for 40 minutes at 70° C. The reaction is cooled to room temperature and concentrated in vacuo. The resulting solid is washed with Et2O and filtered, then placed under high vacuum for 2 hours. The solid is taken up in NH4OH (2 mL) and stirred at room temperature for 1 hour. The reaction mix is concentrated and taken up in 1M HCl. The resulting solid is filtered and rinsed with water to give 66 mg of a white solid (0.18 mmol, 66% yield). 1H NMR (300 MHz, DMSO-D6) δ 12.45 (bs, 1H), 10.18 (bs, 1H), 7.42 (s, 2H), 7.08 (s, 1H), 4.60 (bs, 1H). MS (ESI APCI) positive ion 353 (M+H)+; negative ion 351 (M−H)−.

Workup

customsealed in a reaction tube
temperatureThe reaction is cooled to room temperature
concentrationconcentrated in vacuo
washThe resulting solid is washed with Et2O
filtrationfiltered
waitplaced under high vacuum for 2 hours
stirringstirred at room temperature for 1 hour
additionThe reaction mix
concentrationis concentrated
filtrationThe resulting solid is filtered
washrinsed with water

Sources & evidence

ORD record: ord-f3330f886c4542d281f9de100ed8ae48
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07119205B2

Reaction notes

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