Morpholine → HCID 71280241, compound

HRID 1497929Notes

Reaction equation

HRID 1497929 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:13][C:14]3[CH:19]=[C:18]([C:20]4[N:24]=[C:23]([CH:25]5[CH2:28][C:27]([F:30])([F:29])[CH2:26]5)[O:22][N:21]=4)[CH:17]=[CH:16][C:15]=3[CH3:31])=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+].[NH:84]1[CH2:89][CH2:88][O:87][CH2:86][CH2:85]1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:30][C:27]1([F:29])[CH2:28][CH:25]([C:23]2[O:22][N:21]=[C:20]([C:18]3[CH:17]=[CH:16][C:15]([CH3:31])=[C:14]([NH:13][C:11]([C:8]4[N:5]5[CH:6]=[CH:7][C:2]([N:84]6[CH2:89][CH2:88][O:87][CH2:86][CH2:85]6)=[CH:3][C:4]5=[N:10][CH:9]=4)=[O:12])[CH:19]=3)[N:24]=2)[CH2:26]1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 71280749HCID 71280749, compound

Product 1

HCID 71280241HCID 71280241, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 7-bromo-N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (42f) (50.0 mg, 0.10 mmol), Pd2(dba)3(9.2 mg, 0.01 mmol), rac-BINAP (18.7 mg, 0.03 mmol), NaOt-Bu (14.4 mg, 0.15 mmol) and morphline (17.4 mg, 0.2 mmol) in toluene (3 mL) was heated at 110° C. overnight. Once complete, the reaction mixture was diluted and extracted with EtOAc. The organic layers were combined, dried over Na2SO4, filtered and concentrated to afford a residue which was purified by HPLC to give N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-7-morpholinoimidazo[1,2-a]pyridine-3-carboxamide (F59). MS m/z 495.1 (M+1)+.

Workup

  1. additionOnce complete, the reaction mixture was diluted
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford a residue which
  7. customwas purified by HPLC

Sources & evidence

ORD record
ord-c48de4bce956459cb164c875524a0c0e
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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