HCID 59624586, compound → HCID 178511617, compound

HRID 1943419Notes

Reaction equation

HRID 1943419 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([C:18]2[N:22]3[N:23]=[C:24](Cl)[CH:25]=[C:26]([NH:27][CH:28]4[CH2:30][CH2:29]4)[C:21]3=[N:20][CH:19]=2)=[O:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:32][C@H:33]1[CH2:38][CH2:37][C@H:36]([NH2:39])[CH2:35][CH2:34]1>CO>[NH2:32][C@H:33]1[CH2:38][CH2:37][C@H:36]([NH:39][C:24]2[CH:25]=[C:26]([NH:27][CH:28]3[CH2:30][CH2:29]3)[C:21]3[N:22]([C:18]([C:16]([NH:15][C:11]4[CH:10]=[C:9]([O:8][CH2:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)[N:14]=[CH:13][N:12]=4)=[O:17])=[CH:19][N:20]=3)[N:23]=2)[CH2:35][CH2:34]1

Participants

4

Reactant 2

HCID 59624586HCID 59624586, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178511617HCID 178511617, compoundYield 44.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(6-(benzyloxy)pyrimidin-4-yl)-6-chloro-8-(cyclopropylamino)imidazo[1,2-b]pyridazine-3-carboxamide (70 mg, 0.161 mmol) and trans-1,4-diaminocyclohexane (367 mg, 3.21 mmol) were heated at 160° C. for 2 hrs. The reaction mixture was diluted with methanol and purified by preparative HPLC (Phenomenex Axia Luna 5 micron 30×100 mm) 10% B (Solvent B=90% MeOH-10% H2O-0.1% TFA) to 100% B in A (Solvent A=10% MeOH-90% H2O-0.1% TFA)) to isolate 6-((trans)-4-aminocyclohexylamino)-N-(6-(benzyloxy)pyrimidin-4-yl)-8-(cyclopropylamino)imidazo[1,2-b]pyridazine-3-carboxamide (37 mg, 0.072 mmol, 44.9% yield) as light yellow solid. LC/MS (Phenomenex Luna 5 micron C18 4.6×30 mm, 0 to 100 B in 2 min with 1 min hold time, Flow rate=5 mL/min, detection at 254 nm, Solvent A: 10% methanol/90% water/0.1% TFA; Solvent B: 10% water/90% methanol/0.1% TFA) Rt=1.818 (M+H=514.25).

Workup

  1. custompurified by preparative HPLC (Phenomenex Axia Luna 5 micron 30×100 mm) 10% B (Solvent B=90% MeOH-10% H2O-0.1% TFA) to 100% B in A (Solvent A=10% MeOH-90% H2O-0.1% TFA))

Sources & evidence

ORD record
ord-a245aa71270b40beba546729e9cdec67
Source dataset
uspto-grants-2013_03
Patent number
US08389527B2

Reaction notes

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