3-Bromo-6-fluoroimidazo[1,2-b]pyridazine → HCID 86696455, compound

HRID 870750Notes

Reaction equation

HRID 870750 reaction equation
[Br:1][C:2]1[N:6]2[N:7]=[C:8](F)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[NH2:12][CH2:13][C@H:14]1[N:18]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:17](=[O:24])[CH2:16][CH2:15]1>>[Br:1][C:2]1[N:6]2[N:7]=[C:8]([NH:12][CH2:13][C@H:14]3[N:18]([CH2:19][CH2:20][CH:21]([CH3:22])[CH3:23])[C:17](=[O:24])[CH2:16][CH2:15]3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1

Participants

3

Reactant 2

HCID 866963183-Bromo-6-fluoroimidazo[1,2-b]pyridazineHCID 86696456HCID 86696456, compound

Product 1

HCID 86696455HCID 86696455, compoundYield 60%

Procedure

The 3-bromo-6-fluoroimidazo[1,2-b]pyridazine was reacted with (S)-5-(aminomethyl)-1-isopentylpyrrolidin-2-one under the amine displacement conditions described in example 5.6.42, Part A to afford 60% titled compound. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.95 (d, J=6.32 Hz, 6H) 1.39-1.66 (m, 3H) 1.95-2.08 (m, 1H) 2.13-2.26 (m, 1H) 2.31-2.53 (m, 2H) 3.02 (ddd, J=13.89, 9.22, 4.93 Hz, 1H) 3.48 (dt, J=14.15, 5.18 Hz, 1H) 3.79 (ddd, J=13.77, 9.35, 6.95 Hz, 1H) 3.91 (ddd, J=14.08, 7.01, 2.91 Hz, 1H) 4.00-4.11 (m, 1H) 5.42 (t, J=5.31 Hz, 1H) 6.67 (d, J=9.60 Hz, 1H) 7.52 (s, 1H) 7.66 (d, J=9.85 Hz, 1H); LRMS (ESI) m/380.0 doublet [(M+H)+, calcd for C16H22BrN5O 379.0].

Sources & evidence

ORD record
ord-97380da23e894d218520511640e734af
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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