Ammonia → HCID 70817806, compound

HRID 1501363Notes

Reaction equation

[NH2:1][C:2]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:13]=[C:14]4[C:19]([CH3:20])=[C:18]([CH3:21])[C:17]([C:22]([O:24]C)=O)=[N:16][N:15]4[C:26]=3[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3]1.CO.[NH3:35]>>[NH2:1][C:2]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:13]=[C:14]4[C:19]([CH3:20])=[C:18]([CH3:21])[C:17]([C:22]([NH2:35])=[O:24])=[N:16][N:15]4[C:26]=3[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:8][CH:7]=2)[CH2:3][CH2:4][CH2:5]1

Participants

Reactant 3

HCID 222Ammonia

HCID 887Methanol

HCID 70817949HCID 70817949, compound

Product 1

HCID 70817806HCID 70817806, compoundYield 77%

Conditions

Temperature: 130 °C

Procedure

A solution of methyl 2-[4-(1-aminocyclobutyl)phenyl]-7,8-dimethyl-3-phenylimidazo[1,2-b]pyridazine-6-carboxylate [that was prepared in a manner analgous to that described for Example 51] (80 mg, ˜90% purity, 0.170 mmol, 1.0 eq) in 2.41 ml 7N ammonia in MeOH (˜100 eq of NH3) was heated for 2 hours at 130° C. by the use of a single mode microwave oven (Biotage). On cooling the volatile components were removed in vacuo. The crude mixture was purified via MPLC (Biotage Isolera; 11 g SNAP NH2 cartridge: hexane/EtOAc 1:1→EtOAc) to give 54 mg (77% yield) of the title compound.

Workup

temperatureOn cooling the volatile components
customwere removed in vacuo
customThe crude mixture was purified via MPLC (Biotage Isolera; 11 g SNAP NH2 cartridge: hexane/EtOAc 1:1→EtOAc)

Sources & evidence

ORD record: ord-ef69141d0243433990a3cd44d83d23b9
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206185B2

Reaction notes

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