Potassium Hydroxide → HCID 68291989, compound

HRID 1507950Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[N:8][N:7]2[CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:12]=[C:6]2[C:5]=1[NH:19][CH:20]([CH3:28])[C:21]([CH3:27])([CH3:26])[C:22]([O:24]C)=[O:23])(=[O:3])[NH2:2].[OH-].[K+]>CO.O>[C:1]([C:4]1[CH:9]=[N:8][N:7]2[CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:12]=[C:6]2[C:5]=1[NH:19][CH:20]([CH3:28])[C:21]([CH3:27])([CH3:26])[C:22]([OH:24])=[O:23])(=[O:3])[NH2:2]

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl 3-(3-carbamoyl-6-phenylpyrrolo[1,2-b]pyridazin-4-ylamino)-2,2-dimethylbutanoate (0.2 g, 0.526 mmol) was taken in a mixture of MeOH (30 mL) and water (3 mL). Potassium hydroxide (0.442 g, 7.89 mmol) was added and the reaction mixture was heated at reflux overnight. After completion of the reaction, MeOH was concentrated under reduced pressure and the crude mass was cooled to 0° C. and acidified to pH 5 by stirring in 1.5N HCl solution for 15 min. An off white colored solid separated out which was filtered and dried under vacuum to give the title compound (0.16 g, 83.3% yield). 1H NMR (400 MHz, DMSO-d6): δ 1.22-1.23 (d, J=7.2 Hz, 6H), 1.31-1.32 (d, J=6.4 Hz), 4.70-4.75 (m, 1H), 7.26-7.29 (t, J=6.8 Hz, J=7.2 Hz, 2H), 7.40-7.44 (t, J=7.6, J=7.6 Hz, 2H), 7.78-7.80 (d, J=7.6 Hz, 2H), 8.20-8.23 (d, J=13.2 Hz, 2H), 10.95-10.98 (d, J=9.6 Hz, 1H), 12.45 (s, 1H).

Workup

temperaturethe reaction mixture was heated
temperatureat reflux overnight
concentrationwas concentrated under reduced pressure
customAn off white colored solid separated out which
filtrationwas filtered
customdried under vacuum

Sources & evidence

ORD record: ord-6ed1709f15094759a7b7cefe98e1c68d
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221826B2

Reaction notes

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