Sodium Hydroxide → HCID 24994974, compound

HRID 1972162Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:18]=[C:17]([NH:19][C:20]3[CH:25]=[C:24]([O:26][C:27]4[C:28]([CH3:39])=[N:29][CH:30]=[C:31]([C:37]=4[CH3:38])[C:32]([O:34]CC)=[O:33])[C:23]([Br:40])=[CH:22][N:21]=3)[S:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:18]=[C:17]([NH:19][C:20]3[CH:25]=[C:24]([O:26][C:27]4[C:28]([CH3:39])=[N:29][CH:30]=[C:31]([C:37]=4[CH3:38])[C:32]([OH:34])=[O:33])[C:23]([Br:40])=[CH:22][N:21]=3)[S:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

Ethyl 5-(2-(3-(1-(tert-butoxycarbonyl)piperidin-4-yl)-1,2,4-thiadiazol-5-ylamino)-5-bromopyridin-4-yloxy)-4,6-dimethylnicotinate (prepared according to Example 7; 0.050 g, 0.08 mmol) was dissolved in EtOH (2 mL). NaOH (1N in H2O, 0.28 ml, 0.28 mmol) was added. The reaction stirred at 60° C. for 1 hour. The solution was cooled and concentrated. The material was acidified with saturated NH4Cl solution and extracted with dichloromethane. The organic layer was washed with water, dried and concentrated to give 5-(2-(3-(1-(tert-butoxycarbonyl)piperidin-4-yl)-1,2,4-thiadiazol-5-ylamino)-5-bromopyridin-4-yloxy)-4,6-dimethylnicotinic acid (0.012 g, 25% yield) as an off white solid. 1H NMR (400 MHz, DMSO-d6) δ 1.39 (s, 9H), 1.52-1.55 (m 2H), 1.89-1.93 (m, 2H), 2.34 (s, 6H), 2.84-2.93 (m, 3H), 3.90-3.94 (m, 2H), 6.20 (s, 1H), 8.62 (s, 1H), 8.89 (s, 1H), 11.69 (s, 1H), 13.09 (s, 1H).

Workup

temperatureThe solution was cooled
concentrationconcentrated
extractionextracted with dichloromethane
washThe organic layer was washed with water
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-d32e2834c2b64594a3bd27d7c84de674
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431713B2

Reaction notes

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