Ammonium Hydroxide → HCID 67451721, compound

HRID 869201Notes

Reaction equation

C(OC([N:8]([CH2:24][C:25]1([C:29]2[C:34]([F:35])=[CH:33][CH:32]=[CH:31][N:30]=2)[CH2:28][CH2:27][CH2:26]1)[C:9]1[N:14]=[N:13][C:12]([C:15]2[CH:19]=[C:18]([C:20]([O:22]C)=O)[O:17][N:16]=2)=[CH:11][CH:10]=1)=O)(C)(C)C.[OH-].[NH4+:37]>CO>[F:35][C:34]1[C:29]([C:25]2([CH2:24][NH:8][C:9]3[N:14]=[N:13][C:12]([C:15]4[CH:19]=[C:18]([C:20]([NH2:37])=[O:22])[O:17][N:16]=4)=[CH:11][CH:10]=3)[CH2:28][CH2:27][CH2:26]2)=[N:30][CH:31]=[CH:32][CH:33]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Methyl 3-(6-(tert-butoxycarbonyl((1-(3-fluoropyridin-2-yl)cyclobutyl)methyl)amino)pyridazin-3-yl)isoxazole-5-carboxylate (0.53 g, 1.1 mmol), methanol (5 mL) and concentrated ammonium hydroxide (8 mL) were combined in a microwave reactor and heated to 100° C. for 60 min. The reaction mixture was then concentrated and diluted with EtOAc and washed with satd. aq. NaHCO3 and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated. Resultant oil was diluted in 10 mL of DCM and TFA (6 mL) was added and the reaction was stirred for 35 min. The reaction mixture was then concentrated and purified by reverse phase chromatography to give the title compound as a white solid (144 mg, 36%), (m/z [M+H]=369.1).

Workup

concentrationThe reaction mixture was then concentrated
additiondiluted with EtOAc
washwashed with satd
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
additionResultant oil was diluted in 10 mL of DCM
additionTFA (6 mL) was added
concentrationThe reaction mixture was then concentrated
custompurified by reverse phase chromatography

Sources & evidence

ORD record: ord-2e61c92b26094ce7a3f625f41977eda0
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969346B2

Reaction notes

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