Ammonia → HCID 18416020, compound

HRID 990997Notes

Reaction equation

HRID 990997 reaction equation
[NH:1]1[C:5]2[C:6]3[C:11]([CH2:12][C:4]=2[C:3]([C:13]2[CH:14]=[C:15]([CH:23]=[CH:24][CH:25]=2)[O:16][CH2:17][CH2:18][CH2:19][C:20](O)=[O:21])=[N:2]1)=[CH:10][CH:9]=[CH:8][CH:7]=3.C([N:28](CC)CC)C.ClC(OC)=O.N>O1CCCC1>[NH:1]1[C:5]2[C:6]3[C:11]([CH2:12][C:4]=2[C:3]([C:13]2[CH:14]=[C:15]([CH:23]=[CH:24][CH:25]=2)[O:16][CH2:17][CH2:18][CH2:19][C:20]([NH2:28])=[O:21])=[N:2]1)=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 18415784HCID 18415784, compound

Product 1

HCID 18416020HCID 18416020, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[3-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenoxy]butyric acid (0.24 g) was stirred in dry tetrahydrofuran (5 ml) at ambient temperature and triethylamine (0.20 ml) was added. The mixture was stirred at ambient temperature for 15 minutes then cooled in an ice bath and then methyl chloroformate (0.2 ml) was added. The mixture was stirred at ice bath temperature for 1 hour and then concentrated ammonia solution (SG 0.880, 5 ml) was added dropwise by pipette. The mixture was stirred at 0° C. for 5 minutes and then evaporated to dryness under reduced pressure. The residue was purified by flash column chromatography on silica using dichloromethane/IMS/triethylamine (8:1:1) as the mobile phase. Appropriate fractions were combined and evaporated to give 4-[3-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenoxy]butyramide, m.p. 200-202° C.

Workup

  1. temperaturethen cooled in an ice bath
  2. stirringThe mixture was stirred at ice bath temperature for 1 hour
  3. stirringThe mixture was stirred at 0° C. for 5 minutes
  4. customevaporated to dryness under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica
  6. customevaporated

Sources & evidence

ORD record
ord-75d0a75d02fc4791b1a159b92cb9cf30
Source dataset
uspto-grants-2002_10
Patent number
US06462036B1

Reaction notes

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