Ammonia → HCID 178513556, compound

HRID 869197Notes

Reaction equation

C(OC([N:8]([CH2:25][C:26]1([C:30]2[C:35]([F:36])=[CH:34][CH:33]=[CH:32][N:31]=2)[CH2:29][CH2:28][CH2:27]1)[C:9]1[N:14]=[N:13][C:12]([C:15]2[NH:19][N:18]=[C:17]([C:20]([O:22]CC)=O)[CH:16]=2)=[CH:11][CH:10]=1)=O)(C)(C)C.[NH3:37]>CO>[F:36][C:35]1[C:30]([C:26]2([CH2:25][NH:8][C:9]3[N:14]=[N:13][C:12]([C:15]4[NH:19][N:18]=[C:17]([C:20]([NH2:37])=[O:22])[CH:16]=4)=[CH:11][CH:10]=3)[CH2:29][CH2:28][CH2:27]2)=[N:31][CH:32]=[CH:33][CH:34]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Ethyl 5-(6-(t-butoxycarbonyl((1-(3-fluoropyridin-2-yl)cyclobutyl)methyl)amino)pyridazin-3-yl)-1H-pyrazole-3-carboxylate (0.28 g, 0.56 mmol) and 7N ammonia in MeOH were combined in a microwave reactor and heated to 110° C. for 1 h. The reaction mixture was then concentrated, diluted with EtOAc, and washed with satd. aq. NaHCO3 and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated. The resultant oil was diluted in 10 mL of DCM and TFA (15 mL) was added. The reaction mixture was then concentrated and purified by reverse phase chromatography to give the title compound as a white solid (18 mg, 12%), (m/z [M+H]=368.1).

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
additionThe resultant oil was diluted in 10 mL of DCM
additionTFA (15 mL) was added
concentrationThe reaction mixture was then concentrated
custompurified by reverse phase chromatography

Sources & evidence

ORD record: ord-c2adb423c5534f5fafcc5719e64cd180
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969346B2

Reaction notes

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