1,2-Dichloroethane → HCID 69866036, compound

HRID 2307452Notes

Reaction equation

HRID 2307452 reaction equation
Cl.[N:2]1([C:8]2[CH:9]=[C:10]([C@@H:14]([NH2:16])[CH3:15])[CH:11]=[CH:12][CH:13]=2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[F:17][C:18]1[CH:28]=[CH:27][CH:26]=[CH:25][C:19]=1[CH:20]=[CH:21][C:22](O)=[O:23].C(Cl)CCl.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[F:17][C:18]1[CH:28]=[CH:27][CH:26]=[CH:25][C:19]=1[CH:20]=[CH:21][C:22]([NH:16][C@H:14]([C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([N:2]2[CH2:7][CH2:6][O:5][CH2:4][CH2:3]2)[CH:9]=1)[CH3:15])=[O:23]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 679773-(2-Fluorophenyl)prop-2-enoic acidHCID 69866858HCID 69866858, compound

Product 1

HCID 69866036HCID 69866036, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Mixture of (S)-1-(3-morpholin-4-yl-phenyl)-ethylamine hydrochloride, Preparation 21 (50 mg, 0.21 mmol), 2-fluorocinnamic acid (37 mg, 0.23 mmol), EDC (79 mg, 0.41 mmol), DMAP (25 mg, 0.21 mmol), triethylamine (0.11 ml, 0.82 mmol) in dichloromethane (1 mL) was stirred at room temperature for 10 hours. The reaction mixture was concentrated under vacuum and purified by filtering through 2 g silica-gel syringe with 80% ethyl acetate/hexanes. The filtrate was concentrated under vacuum to provide the title compound as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. custompurified
  3. filtrationby filtering through 2 g silica-gel syringe with 80% ethyl acetate/hexanes
  4. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-a8f299c665c34944bb9ad6c1a00e97db
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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