(+-)-2-Butanol → 1-(2-Fluoro-4-(3-((7-methoxy-1,5-naphthyridin-4-ylamino)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)pyrrolidin-2-one

HRID 40221Notes

Reaction equation

HRID 40221 reaction equation
[NH2:1][CH2:2][C:3]1[N:7]2[N:8]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH2:22][CH2:21][CH2:20][C:19]4=[O:23])=[C:14]([F:24])[CH:13]=3)[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1.Cl[C:26]1[CH:27]=[CH:28][N:29]=[C:30]2[C:35]=1[N:34]=[CH:33][C:32]([O:36][CH3:37])=[CH:31]2.CC(O)CC>>[F:24][C:14]1[CH:13]=[C:12]([C:9]2[CH:10]=[CH:11][C:6]3[N:7]([C:3]([CH2:2][NH:1][C:26]4[C:35]5[C:30](=[CH:31][C:32]([O:36][CH3:37])=[CH:33][N:34]=5)[N:29]=[CH:28][CH:27]=4)=[N:4][N:5]=3)[N:8]=2)[CH:17]=[CH:16][C:15]=1[N:18]1[CH2:22][CH2:21][CH2:20][C:19]1=[O:23]

Participants

4

Reactant 3

HCID 6568(+-)-2-ButanolHCID 576912831-(4-(3-(Aminomethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-2-fluorophenyl)pyrrolidin-2-oneHCID 594273408-Chloro-3-methoxy-1,5-naphthyridine

Product 1

HCID 576912621-(2-Fluoro-4-(3-((7-methoxy-1,5-naphthyridin-4-ylamino)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)pyrrolidin-2-one

Procedure

A 0.5-2 mL microwave vial was charged with 1-(4-(3-(aminomethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-2-fluorophenyl)pyrrolidin-2-one (0.0792 g, 0.243 mmol), 8-chloro-3-methoxy-1,5-naphthyridine (0.0590 g, 0.303 mmol), and butan-2-ol (1.00 ml, 0.243 mmol), sealed, then placed in a Personal Chemistry Microwave for 4 hours at 120° C. The mixture was concentrated, then triturated with MeOH to give 1-(2-fluoro-4-(3-((7-methoxy-1,5-naphthyridin-4-ylamino)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)pyrrolidin-2-one as the hydrochloric salt.

Workup

  1. customsealed
  2. concentrationThe mixture was concentrated
  3. customtriturated with MeOH

Sources & evidence

ORD record
ord-705e2140155f4f7a97af4e822843e8d9
Source dataset
uspto-grants-2013_09
Patent number
US08524900B2

Reaction notes

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