HCID 59624627, compound → HCID 178490938, compound

HRID 1943482Notes

Reaction equation

HRID 1943482 reaction equation
Cl[C:2]1[CH:3]=[C:4]([N:21]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[C:5]2[N:6]([C:8]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][N:17]=[C:16]([F:20])[CH:15]=3)=[O:12])=[CH:9][N:10]=2)[N:7]=1.[C@H:37]1([NH2:44])[CH2:42][CH2:41][C@H:40]([NH2:43])[CH2:39][CH2:38]1>CN1C(=O)CCC1>[NH2:43][C@H:40]1[CH2:41][CH2:42][C@H:37]([NH:44][C:2]2[CH:3]=[C:4]([N:21]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[C:5]3[N:6]([C:8]([C:11]([NH:13][C:14]4[CH:19]=[CH:18][N:17]=[C:16]([F:20])[CH:15]=4)=[O:12])=[CH:9][N:10]=3)[N:7]=2)[CH2:38][CH2:39]1

Participants

4

Reactant 2

HCID 59624627HCID 59624627, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178490938HCID 178490938, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 6-chloro-N-(2-fluoropyridin-4-yl)-8-((4-methoxybenzyl)(pyridin-2-yl)amino)imidazo[1,2-b]pyridazine-3-carboxamide (60 mg, 0.119 mmol) and (trans)-cyclohexane-1,4-diamine (136 mg, 1.191 mmol) in NMP (1 mL) was heated at 90° C. for 8 h and then cooled to room temperature. The crude reaction mixture was purified by preparative HPLC (Phenomenex Axia Luna 5 micron 30×100 mm) to obtain the pure product as a white solid, which was used without further purification.

Workup

  1. customThe crude reaction mixture
  2. customwas purified by preparative HPLC (Phenomenex Axia Luna 5 micron 30×100 mm)

Sources & evidence

ORD record
ord-bd9fb5cb99444fb38e1f27fb359ddb1e
Source dataset
uspto-grants-2013_03
Patent number
US08389527B2

Reaction notes

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