1,1'-Carbonyldiimidazole → HCID 178517423, compound

HRID 2201424Notes

Reaction equation

HRID 2201424 reaction equation
[OH:1][NH:2][C:3](=[NH:21])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([OH:20])[CH:16]=3)[N:11]=2)=[CH:6][CH:5]=1.C1N=CN([C:27](N2C=NC=C2)=[O:28])C=1>C1COCC1>[OH:20][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([C:7]1[CH:6]=[CH:5][C:4]([C:3]3[NH:2][O:1][C:27](=[O:28])[N:21]=3)=[CH:9][CH:8]=1)[CH:19]=[CH:18]2

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178513258HCID 178513258, compound

Product 1

HCID 178517423HCID 178517423, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

N-hydroxy-4-(6-hydroxyquinolin-2-yl)benzimidamide (800 mg, 2.86 mmol) was dissolved in 25 mL of THF and CDI (557 mg, 3.44 mmol) and TEA (0.2 mL) was added. The mixture was stirred at 65° C. for 2 hours, followed by concentration in vacuo. The crude material was dissolved in 10 mL 1N NaOH and filtered through Celite. The mixture was then acidified with 1N HCl to a pH of 4.5 and the solids were filtered and dried. The solids were slurried in 10 mL of EtOAc overnight at 50° C. followed by filtration to yield Compound IV-12 (315 mg, 36% yield). 1H NMR (DMSO-d6, 400 MHz): δ 10.19 (s, 1H), 8.42 (d, 2H), 8.28 (d, 1H), 8.14-8.11 (d, 1H), 8.00-7.94 (m, 3H), 7.39-7.35 (dd, 1H), 7.21 (s, 1H). MS (ESI): m/z 306.44 [M+H]+.

Workup

  1. concentrationfollowed by concentration in vacuo
  2. dissolutionThe crude material was dissolved in 10 mL 1N NaOH
  3. filtrationfiltered through Celite
  4. filtrationthe solids were filtered
  5. customdried
  6. waitThe solids were slurried in 10 mL of EtOAc overnight at 50° C.
  7. filtrationfollowed by filtration
  8. customto yield Compound IV-12 (315 mg, 36% yield)

Sources & evidence

ORD record
ord-6a0d23ddd1be4d608106290f6af6f111
Source dataset
uspto-grants-2016_06
Patent number
US09364481B2

Reaction notes

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