(4-(Aminomethyl)phenyl)boronic acid → 1-{3-[3-(4-Aminomethyl-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-propyl}-pyrrolidin-2-one

HRID 870664Notes

Reaction equation

HRID 870664 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][C:16]3=[O:20])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[NH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1>>[NH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:2]2[N:6]3[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][N:15]4[CH2:19][CH2:18][CH2:17][C:16]4=[O:20])[CH:9]=[CH:10][C:5]3=[N:4][CH:3]=2)=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 2734312(4-(Aminomethyl)phenyl)boronic acidHCID 686481591-(3-(3-Bromoimidazo[1,2-b]pyridazin-6-ylamino)propyl)pyrrolidin-2-one

Product 1

HCID 866963631-{3-[3-(4-Aminomethyl-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-propyl}-pyrrolidin-2-oneYield 64%

Procedure

The 1-(3-((3-bromoimidazo[1,2-b]pyridazin-6-yl)amino)propyl)pyrrolidin-2-one was also coupled to (4-(aminomethyl)phenyl)boronic acid using the Suzuki coupling conditions described in example 5.6.19 to obtain the titled product in 64% yield. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.94-2.09 (m, 4H) 2.33-2.43 (m, 2H) 3.36-3.53 (m, 6H) 4.16 (s, 2H) 6.74 (d, J=9.60 Hz, 1H) 7.57 (m, J=8.34 Hz, 2H) 7.65 (d, J=9.60 Hz, 1H) 7.81 (s, 1H) 8.25 (m, J=8.34 Hz, 2H); LRMS (ESI) m/e 365.0 [(M+H)+, calcd for C20H24N6O 364.0].

Sources & evidence

ORD record
ord-01c32896d56a417094fb99e8004c6da4
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

Loading…