1,2-Dichloroethane → HCID 69852395, compound

HRID 2307457Notes

Reaction equation

HRID 2307457 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][C@@H:9]1[O:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([NH2:23])[CH3:22])[CH:16]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[F:25][C:26]1[CH:27]=[C:28]([CH:34]=[CH:35][C:36]=1[F:37])[CH:29]=[CH:30][C:31](O)=[O:32].C(Cl)CCl.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][C@@H:9]1[O:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([NH:23][C:31](=[O:32])[CH:30]=[CH:29][C:28]3[CH:34]=[CH:35][C:36]([F:37])=[C:26]([F:25])[CH:27]=3)[CH3:22])[CH:16]=2)[CH2:10]1)([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 1454863-(3,4-Difluorophenyl)prop-2-enoic acidHCID 69852259HCID 69852259, compound

Product 1

HCID 69852395HCID 69852395, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Mixture of (S)-{4-[3-(1-amino-ethyl)-phenyl]-morpholin-2-ylmethyl}-carbamic acid tert-butyl ester, Preparation 28 (20 mg, 0.06 mmol), 3,4-difluorocinnamic acid (12.1 mg, 0.07 mmol), EDC (23 mg, 0.12 mmol), DMAP (7.3 mg, 0.06 mmol), triethylamine (0.03 ml, 0.24 mmol) in dichloromethane (0.6 ml) was stirred at room temperature overnight. The reaction mixture was 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. customThe reaction mixture was purified
  2. filtrationby filtering through 2 g silica-gel syringe with 80% ethyl acetate/hexanes
  3. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-398d7a5e61c44cf5871655c4dec9d212
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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