1,2-Dichloroethane → HCID 69919811, compound

HRID 2307453Notes

Reaction equation

HRID 2307453 reaction equation
Cl.[CH3:2][C@H:3]1[O:8][C@@H:7]([CH3:9])[CH2:6][N:5]([C:10]2[CH:11]=[C:12]([C@@H:16]([NH2:18])[CH3:17])[CH:13]=[CH:14][CH:15]=2)[CH2:4]1.[F:19][C:20]1[CH:30]=[CH:29][CH:28]=[CH:27][C:21]=1[CH:22]=[CH:23][C:24](O)=[O:25].C(Cl)CCl.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[CH3:9][C@H:7]1[O:8][C@@H:3]([CH3:2])[CH2:4][N:5]([C:10]2[CH:11]=[C:12]([C@@H:16]([NH:18][C:24](=[O:25])[CH:23]=[CH:22][C:21]3[CH:27]=[CH:28][CH:29]=[CH:30][C:20]=3[F:19])[CH3:17])[CH:13]=[CH:14][CH:15]=2)[CH2:6]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 679773-(2-Fluorophenyl)prop-2-enoic acidHCID 69863681HCID 69863681, compound

Product 1

HCID 69919811HCID 69919811, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Mixture of (S)-1-[3-(cis-2,6-dimethyl-morpholin-4-yl)-phenyl]-ethylamine hydrochloric acid salt, Preparation 31 (50 mg, 0.16 mmol), 2-fluorocinnamic acid (30 mg, 0.18 mmol), EDC (65 mg, 0.33 mmol), DMAP (20 mg, 0.16 mmol), triethylamine (0.09 ml, 0.65 mmol) in dichloromethane (0.7 mL) was stirred at room temperature overnight. The reaction mixture was purified by filtering through 2 g silica-gel syringe with 70% ethyl acetate/hexanes. The filtrate was concentrated under vacuum to provide the title compound as a white solid.

Workup

  1. customThe reaction mixture was purified
  2. filtrationby filtering through 2 g silica-gel syringe with 70% ethyl acetate/hexanes
  3. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-a2b5e42fec634d4ca6c19c9151538979
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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