Hydrochloric Acid → HCID 178468633, compound

HRID 869196Notes

Reaction equation

[C:1]([C:4]1[N:9]=[N:8][C:7]([N:10]([CH2:18][C:19]2([C:23]3[C:28]([F:29])=[CH:27][CH:26]=[CH:25][N:24]=3)[CH2:22][CH2:21][CH2:20]2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:6][CH:5]=1)(=O)[CH3:2].CC[O-].[Na+].[C:34](OCC)(=O)[C:35]([O:37][CH2:38][CH3:39])=[O:36].Cl.[NH2:45][NH2:46]>C1COCC1>[C:13]([O:12][C:11]([N:10]([CH2:18][C:19]1([C:23]2[C:28]([F:29])=[CH:27][CH:26]=[CH:25][N:24]=2)[CH2:22][CH2:21][CH2:20]1)[C:7]1[N:8]=[N:9][C:4]([C:1]2[NH:46][N:45]=[C:34]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:2]=2)=[CH:5][CH:6]=1)=[O:17])([CH3:15])([CH3:16])[CH3:14]

Participants

Conditions

Temperature: 45 °C

Procedure

t-Butyl 6-acetylpyridazin-3-yl((1-(3-fluoropyridin-2-yl)cyclobutyl)methyl)carbamate (2.5 g, 6.2 mmol) in THF (150 mL) was treated with NaOEt (3.44 g, 10.6 mmol, 21% in EtOH). The resulting mixture was then treated with diethyl oxalate (1.7 mL, 12.5 mmol), heated to 45° C., and stirred for 4 h. The reaction mixture was added to 1N HCl, extracted with EtOAc, and washed with satd. aq. NaHCO3 and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated. A portion of the resultant oil was dissolved in AcOH and hydrazine (0.41 g, 13.2 mmol) was added and stirred at 80° C. Concentration afforded a yellow oil which was purified by reverse-phase chromatography to give solid (0.285 g, 62%), (m/z [M+H]=497.2).

Workup

extractionextracted with EtOAc
washwashed with satd
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
dissolutionA portion of the resultant oil was dissolved in AcOH
stirringstirred at 80° C
concentrationConcentration
customafforded a yellow oil which
customwas purified by reverse-phase chromatography

Sources & evidence

ORD record: ord-036c97a54bf3476d9ffbc57461582db2
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969346B2

Reaction notes

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