IRE1|A kinase-IN-9 → 4-(7-Hydroxy-4-methyl-2-oxo-2H-chromen-3-yl)-N-(2-morpholinoethyl)benzamide

HRID 579470Notes

Reaction equation

HRID 579470 reaction equation
C([C:3]1[C:4]([OH:32])=[CH:5][CH:6]=[C:7]2[C:12]=1[O:11][C:10](=[O:13])[C:9]([C:14]1[CH:30]=[CH:29][C:17]([C:18]([NH:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[O:19])=[CH:16][CH:15]=1)=[C:8]2[CH3:31])=O.OC1C=CC2N=C(C3C=CC(C(N4CCN(C)CC4)=O)=CC=3)C=CC=2C=1C=O>CS(O)(=O)=O>[OH:32][C:4]1[CH:3]=[C:12]2[C:7]([C:8]([CH3:31])=[C:9]([C:14]3[CH:15]=[CH:16][C:17]([C:18]([NH:20][CH2:21][CH2:22][N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)=[O:19])=[CH:29][CH:30]=3)[C:10](=[O:13])[O:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 54575078IRE1|A kinase-IN-9HCID 545759296-Hydroxy-2-(4-(4-methylpiperazine-1-carbonyl)phenyl)quinoline-5-carbaldehyde

Product 1

HCID 866834274-(7-Hydroxy-4-methyl-2-oxo-2H-chromen-3-yl)-N-(2-morpholinoethyl)benzamideYield 18%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

Compound 4 (5 g, 21.2 mmol) and compound 5 (5.6 g, 24.3 mmol) were stirred at 0° C. CH3SO3H (50 mL) was added dropwise. Then the mixture was stirred at RT for 16 h. The reaction mixture was poured into crush ice, extracted by DCM. The DCM layer was washed with sat.Na2HPO4, dried over Na2SO4, filtered, concentrated. The residue was purified by silica gel column (DCM:EtOH=50:1), afforded compound 6 (1.2 g, 18%) as light yellow solid.

Workup

  1. additionThe reaction mixture was poured
  2. custominto crush ice
  3. extractionextracted by DCM
  4. washThe DCM layer was washed
  5. dry with materialNa2HPO4, dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column (DCM:EtOH=50:1)

Sources & evidence

ORD record
ord-06b1eb6e9601490a959bbc76692d636d
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

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