1,1'-Carbonyldiimidazole → HCID 178517423, compound

HRID 55792Notes

Reaction equation

HRID 55792 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 36.1%

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 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

Sources & evidence

ORD record
ord-d50b67254d9d4de9bce619ba8a3613db
Source dataset
uspto-grants-2016_09
Patent number
US09433618B2

Reaction notes

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