Acetyl chloride → 3-(4-(aminomethyl)-3-fluorophenyl)-N-butylimidazo[1,2-b]pyridazin-6-amine HCl salt

HRID 870658Notes

Reaction equation

[CH2:1]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([C:15]3[CH:29]=[CH:28][C:18]([CH2:19][NH:20]C(=O)OC(C)(C)C)=[C:17]([F:30])[CH:16]=3)=[CH:13][N:14]=2)[N:11]=1)[CH2:2][CH2:3][CH3:4].C([Cl:34])(=O)C>>[ClH:34].[NH2:20][CH2:19][C:18]1[CH:28]=[CH:29][C:15]([C:12]2[N:10]3[N:11]=[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])[CH:7]=[CH:8][C:9]3=[N:14][CH:13]=2)=[CH:16][C:17]=1[F:30]

Participants

Reactant 2

HCID 6367Acetyl chloride

HCID 86696354Tert-butyl 4-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)-2-fluorobenzylcarbamate

Product 1

HCID 866963553-(4-(aminomethyl)-3-fluorophenyl)-N-butylimidazo[1,2-b]pyridazin-6-amine HCl saltYield 97.4%

Procedure

The solution of tert-butyl 4-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)-2-fluorobenzylcarbamate (91 mg, 0.22 mmol) was cooled to 0° C. and treated with acetyl chloride (518 mg, 6.6 mmol). The reaction was maintained at room temperature for overnight. The resulting solution was concentrated under reduced pressure to afford 3-(4-(aminomethyl)-3-fluorophenyl)-N-butylimidazo[1,2-b]pyridazin-6-amine HCl salt (75 mg, 88% yield) as a white solid: 1H NMR (METHANOL-d4) δ: 8.38 (s, 1H), 8.23 (d, J=11.4 Hz, 1H), 8.05 (d, J=7.8 Hz, 1H), 8.00 (d, J=9.9 Hz, 1H), 7.74 (t, J=7.8 Hz, 1H), 7.30 (d, J=9.9 Hz, 1H), 4.31 (s, 2H), 3.43 (t, J=7.1 Hz, 2H), 1.65-1.84 (m, 2H), 1.42-1.59 (m, 2H), 1.01 (t, J=7.3 Hz, 3H); LRMS (ESI) m/e 314.4 [(M+H)+, calcd for C17H21FN5 314.2].

Workup

concentrationThe resulting solution was concentrated under reduced pressure

Sources & evidence

ORD record: ord-5c2512d07a384e6880f519913adf4838
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969565B2

Reaction notes

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