4-Nitrophenol → HCID 66592549, compound

HRID 1091874Notes

Reaction equation

HRID 1091874 reaction equation
[F:1][CH:2]([F:23])[O:3][C:4]1[C:9]2[O:10][C:11]3[C:12](=[O:19])[N:13]([CH2:17][CH3:18])[N:14]=[CH:15][C:16]=3[C:8]=2[C:7]([C:20]([OH:22])=[O:21])=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH:31]1[C:36]([N+:37]([O-:39])=[O:38])=[CH:35][CH:34]=[C:33](O)[CH:32]=1.CCN=C=NCCCN(C)C>O1CCCC1>[F:23][CH:2]([F:1])[O:3][C:4]1[C:9]2[O:10][C:11]3[C:12](=[O:19])[N:13]([CH2:17][CH3:18])[N:14]=[CH:15][C:16]=3[C:8]=2[C:7]([C:20]([O:22][C:33]2[CH:32]=[CH:31][C:36]([N+:37]([O-:39])=[O:38])=[CH:35][CH:34]=2)=[O:21])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66592658HCID 66592658, compound

Product 1

HCID 66592549HCID 66592549, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-difluoromethoxy-3-ethyl-4-oxo-3,4-dihydrobenzo[4,5]furo[2,3-d]pyridazine-9-carboxylic acid (form step II) (90 mg, 0.276 mmol), triethyl amine (41 mg, 0.415 mmol), p-nitro phenol (43 mg, 0.304 mmol) and EDCI (79 mg, 0.415 mmol) in tetrahydrofuran (3 ml) was stirred at room temp for 16-17 hrs. Progress of reaction was monitored by TLC. At the end, reaction mixture was concentrated under vacuum. Then water (50 ml) was added to reaction mixture and acidified with dilute HCl. The precipitate obtained was filtered and dried in oven. 87 mg buff colored solid was obtained.

Workup

  1. customProgress of reaction
  2. customAt the end, reaction mixture
  3. concentrationwas concentrated under vacuum
  4. additionThen water (50 ml) was added to reaction mixture
  5. customThe precipitate obtained
  6. filtrationwas filtered
  7. customdried in oven
  8. custom87 mg buff colored solid was obtained

Sources & evidence

ORD record
ord-3bb0ba83fd7849dc977466757f08482d
Source dataset
uspto-grants-2012_03
Patent number
US08129401B2

Reaction notes

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