Trifluoroacetic acid → 6-(3-aminopiperidin-1-yl)-N-(5,6-dimethoxypyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine trifluoroacetate

HRID 1755396Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:11][C:12]2[C:13]3[N:14]([CH:32]=[CH:33][N:34]=3)[N:15]=[C:16]([N:18]3[CH2:23][CH2:22][CH2:21][CH:20]([NH:24]C(=O)OC(C)(C)C)[CH2:19]3)[CH:17]=2)=[N:7][C:8]=1[O:9][CH3:10].[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]>ClCCl>[F:38][C:37]([F:40])([F:39])[C:35]([OH:41])=[O:36].[NH2:24][CH:20]1[CH2:21][CH2:22][CH2:23][N:18]([C:16]2[CH:17]=[C:12]([NH:11][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:8]([O:9][CH3:10])[N:7]=3)[C:13]3[N:14]([CH:32]=[CH:33][N:34]=3)[N:15]=2)[CH2:19]1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of tert-butyl 1-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)piperidin-3-ylcarbamate (300 mg, 0.64 mmol) and TFA (5 mL) in dichloromethane (5 mL) was stirred at 25° C. for 6 h. The residue was concentrated to give the crude 6-(3-aminopiperidin-1-yl)-N-(5,6-dimethoxypyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine trifluoroacetate salt (350 mg, crude) as a brown liquid that was used directly without further purification. LC-MS: 370 [M+1]+, tR=1.09 min

Workup

concentrationThe residue was concentrated

Sources & evidence

ORD record: ord-ac118dde38b24c9fa29fc08a5f1903cf
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169259B2

Reaction notes

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