(4-(Aminomethyl)phenyl)boronic acid → 4-((3-(4-(Aminomethyl)phenyl)imidazo[1,2-b]pyridazin-6-yl)amino)-2-methylbutan-2-ol

HRID 870707Notes

Reaction equation

HRID 870707 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[NH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1>>[NH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[N:6]3[N:7]=[C:8]([NH:11][CH2:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15])[CH:9]=[CH:10][C:5]3=[N:4][CH:3]=2)=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 2734312(4-(Aminomethyl)phenyl)boronic acidHCID 866964084-((3-Bromoimidazo[1,2-b]pyridazin-6-yl)amino)-2-methylbutan-2-ol

Product 1

HCID 866964094-((3-(4-(Aminomethyl)phenyl)imidazo[1,2-b]pyridazin-6-yl)amino)-2-methylbutan-2-olYield 78%

Procedure

The 4-((3-bromoimidazo[1,2-b]pyridazin-6-yl)amino)-2-methylbutan-2-ol was coupled with (4-(aminomethyl)phenyl)boronic acid as described in example 5.6.19 to afford the titled compound in 78% yield. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.29 (s, 6H) 1.84-1.94 (m, 2H) 3.49-3.58 (m, 2H) 4.24 (s, 2H) 7.25 (d, J=9.85 Hz, 1H) 7.67 (d, J=8.59 Hz, 2H) 7.97 (d, J=9.85 Hz, 1H) 8.22-8.29 (m, 3H); LRMS (ESI) m/e 326.0 [(M+H)+, calcd for C18H23N5O 325.0].

Sources & evidence

ORD record
ord-a85f4fefdfd24da78df48aa92dd77a54
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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