Water → HCID 48474139, compound

HRID 1435066Notes

Reaction equation

HRID 1435066 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[F:11].CCN=C=NCCCN(C)C.Cl.[CH2:24]([NH2:29])[CH2:25][CH:26]([CH3:28])[CH3:27].O>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:29][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])=[O:8])=[CH:4][C:3]=1[F:11]

Participants

6

Reactant 4

HCID 962WaterHCID 7894IsoamylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27733414-Bromo-3-fluorobenzoic acid

Product 1

HCID 48474139HCID 48474139, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Bromo-3-fluorobenzoic acid (2.00 g, 9.13 mmol) was dissolved in dichloromethane (20 mL) and cooled in an ice/water bath as EDCl (2.10 g, 10.9 mmol) was added. After addition, the reaction mixture was allowed to warm to ambient temperature and stirred for 30 minutes before adding isoamylamine (1.59 g, 18.3 mmol). After 12 hours, water was added and the reaction mixture was extracted with ethyl ether. The combined organic layers were washed sequentially with 1N HCl, 1N NaOH and brine. The organic phase was dried over sodium sulfate, filtered and concentrated. The resulting residue was purified by chromatography on silica gel eluting with 5% ethyl acetate in heptane to afford the title compound (I-5a).

Workup

  1. additionwas added
  2. additionAfter addition
  3. waitAfter 12 hours
  4. extractionthe reaction mixture was extracted with ethyl ether
  5. washThe combined organic layers were washed sequentially with 1N HCl, 1N NaOH and brine
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was purified by chromatography on silica gel eluting with 5% ethyl acetate in heptane

Sources & evidence

ORD record
ord-c12a56ad88f94a638c594d9ccc85c377
Source dataset
uspto-grants-2009_11
Patent number
US07615651B2

Reaction notes

Loading…