Triethylamine → HCID 69918815, compound

HRID 2307468Notes

Reaction equation

HRID 2307468 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][C:10]([OH:12])=O.C(C#N)(Cl)(Cl)Cl.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OC([N:45]1[C:54]2[C:49](=[CH:50][CH:51]=[C:52]([CH:55]([NH2:57])[CH3:56])[CH:53]=2)[CH2:48][CH2:47][CH2:46]1)=O)(C)(C)C.C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][C:10]([NH:57][CH:55]([C:52]1[CH:53]=[C:54]2[C:49]([CH2:48][CH2:47][CH2:46][NH:45]2)=[CH:50][CH:51]=1)[CH3:56])=[O:12]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 11011TrichloroacetonitrileHCID 11776TriphenylphosphineHCID 679773-(2-Fluorophenyl)prop-2-enoic acidHCID 69918840HCID 69918840, compound

Product 1

HCID 69918815HCID 69918815, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(2-fluoro-phenyl)-acrylic acid (166 mg, 1 mmol), CCl3CN (289 mg, 2 mmol) and PPh3 (52 mg, 2 mmol) in CH2Cl2 (10 mL) was stirred at 23° C. for 1.5 hours. Then 7-(1-amino-ethyl)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester, Preparation 29 (276 mg, 1 mmol) was introduced followed by triethylamine (304 mg, 3 mmol). After stirring for 1 hour, the solvent was evaporated, the residue was re-dissolved in a mixture of MeOH (5 mL) and 1M HCl in Et2O (5 mL), and stirred at 23° C. for 24 hours. The solvent was evaporated and the residual material was partitioned between EtOAc and aqueous NaHCO3. The organic phase was washed with water, dried (MgSO4) and evaporated. The crude product was purified by chromatography (SiO2, 10-50% EtOAc in hexane) to give 267 mg (82%) of the title compound as a tan solid.

Workup

  1. additionwas introduced
  2. customthe solvent was evaporated
  3. dissolutionthe residue was re-dissolved in a mixture of MeOH (5 mL) and 1M HCl in Et2O (5 mL)
  4. stirringstirred at 23° C. for 24 hours
  5. customThe solvent was evaporated
  6. customthe residual material was partitioned between EtOAc and aqueous NaHCO3
  7. washThe organic phase was washed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customThe crude product was purified by chromatography (SiO2, 10-50% EtOAc in hexane)

Sources & evidence

ORD record
ord-aabab74a3fbf47498ac07693c6ef4d65
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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