Morpholine → 6-(2,4-Dichloro-phenyl)-8-isobutoxy-3-(6-morpholin-4-yl-pyridin-3-yl)-imidazo[1,2-a]pyridine-7-carbonitrile

HRID 420539Notes

Reaction equation

HRID 420539 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:30]#[N:31])=[C:11]([O:25][CH2:26][CH:27]([CH3:29])[CH3:28])[C:12]2[N:13]([C:15]([C:18]3[CH:19]=[N:20][C:21](F)=[CH:22][CH:23]=3)=[CH:16][N:17]=2)[CH:14]=1.[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>CS(C)=O.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:30]#[N:31])=[C:11]([O:25][CH2:26][CH:27]([CH3:29])[CH3:28])[C:12]2[N:13]([C:15]([C:18]3[CH:19]=[N:20][C:21]([N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)=[CH:22][CH:23]=3)=[CH:16][N:17]=2)[CH:14]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 666590186-(2,4-Dichloro-phenyl)-3-(6-fluoro-pyridin-3-yl)-8-isobutoxy-imidazo[1,2-a]pyridine-7-carbonitrile

Product 1

HCID 666591956-(2,4-Dichloro-phenyl)-8-isobutoxy-3-(6-morpholin-4-yl-pyridin-3-yl)-imidazo[1,2-a]pyridine-7-carbonitrileYield 92.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 6-(2,4-dichloro-phenyl)-3-(6-fluoro-pyridin-3-yl)-8-isobutoxy-imidazo[1,2-a]pyridine-7-carbonitrile (64 mg, 0.14 mmol) and morpholine (0.06 mL, 0.70 mmol) in DMSO (1 mL) was heated at 180° C. and stirred for 30 min. The reaction mixture was cooled to RT, diluted in AcOEt (20 mL) and washed with water (2×10 ml). The organic layer was dried over Na2SO4, filtered, and evaporated to dryness to yield the crude 6-(2,4-dichloro-phenyl)-8-isobutoxy-3-(6-morpholin-4-yl-pyridin-3-yl)-imidazo[1,2-a]pyridine-7-carbonitrile intermediate (67.8 mg) as a brown solid.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. washwashed with water (2×10 ml)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-dd35874527be4d79baf3c8ea2f0083e8
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

Loading…