HCID 54689858, compound → HCID 54689877, compound

HRID 1244153Notes

Reaction equation

C([O:8][C:9]1[C:14]([Br: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[Br:29])C1C=CC=CC=1>Br.CC(O)=O>[Br: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]([Br:15])[C:9]=1[OH:8]

Participants

Conditions

Temperature: 70 °C

Procedure

The 3-(4-benzyloxy-3,5-dibromo-phenyl)-4-hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile from Example 36e (150 mg, 0.281 mmol) was dissolved in 30% HBr/AcOH (2 mL) and sealed in a reaction tube with stirring for 30 min 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 to remove remaining acid. The solid is then taken up in NH4OH (2 mL) and stirred at room temperature for 20 minutes. The reaction mix is concentrated and taken up in 1M HCl. The resulting solid is filtered and rinsed with water to give 75 mg of a green solid as the titled compound (0.169 mmol, 60% yield). 1H NMR (300 MHz, DMSO-d6) δ 12.54 (bs, 1H), 9.98 (bs, 1H), 7.59 (s, 2H), 7.09 (s, 1H), 4.13 (bs, 1H). MS (ESI APCI) m/e 442 (M+H)+; 440 (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
customto remove
stirringstirred at room temperature for 20 minutes
additionThe reaction mix
concentrationis concentrated
filtrationThe resulting solid is filtered
washrinsed with water

Sources & evidence

ORD record: ord-d1c9d2e821af47958c6772ee7759ca1c
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07119205B2

Reaction notes

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