Carbon Dioxide → 6-(2,4-Dichloro-phenyl)-8-isobutylamino-3-morpholin-4-yl-imidazo[1,2-a]pyridine-7-carbonitrile

HRID 420526Notes

Reaction equation

HRID 420526 reaction equation
Cl[C:2]1[C:3]2[N:4]([C:18]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[CH:19][N:20]=2)[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[C:7]=1[C:8]#[N:9].[CH2:27]([NH2:31])[CH:28]([CH3:30])[CH3:29].C(=O)=O>O1CCOCC1>[Cl:17][C:11]1[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:10]=1[C:6]1[C:7]([C:8]#[N:9])=[C:2]([NH:31][CH2:27][CH:28]([CH3:30])[CH3:29])[C:3]2[N:4]([C:18]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[CH:19][N:20]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 6558IsobutylamineHCID 66658969HCID 66658969, compound

Product 1

HCID 666590356-(2,4-Dichloro-phenyl)-8-isobutylamino-3-morpholin-4-yl-imidazo[1,2-a]pyridine-7-carbonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a sealed tube, a solution of 8-chloro-6-(2,4-dichloro-phenyl)-3-morpholin-4-yl-imidazo[1,2-a]pyridine-7-carbonitrile (30 mg, 0.074 mmol) and isobutylamine (0.044 mL, 0.44 mmol) in dioxane (1 mL) was heated at 110° C. for 14 h. The reaction mixture was cooled to RT, then frozen at −44° C. (dry ice) and lyophilized to give the crude 6-(2,4-dichloro-phenyl)-8-isobutylamino-3-morpholin-4-yl-imidazo[1,2-a]pyridine-7-carbonitrile intermediate. HPLC: AtRet=2.77.

Sources & evidence

ORD record
ord-b65f22dbe2844f2387f73e489981fe91
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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