1,2-Dichloroethane → HCID 69917136, compound

HRID 2307474Notes

Reaction equation

HRID 2307474 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=O)=[CH:4][CH:3]=1.[CH3:13][N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:21]=[C:22]([C@@H:26]([NH2:28])[CH3:27])[CH:23]=[CH:24][CH:25]=2)[CH2:16][CH2:15]1.C(Cl)CCl.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][C:8]([NH:28][C@H:26]([C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([N:17]3[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH2:16]3)[CH:21]=2)[CH3:27])=[O:10])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 980703-(4-Fluorophenyl)-2-propenoic acidHCID 59095725HCID 59095725, compound

Product 1

HCID 69917136HCID 69917136, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-fluorocinnamic acid (17 mg, 0.1 mmol), (S)-1-[3-(4-methylpiperazin-1-yl)-phenyl]ethylamine (preparation 42, 24 mg, 0.11 mmol), EDC (28 mg, 0.15 mmol), DMAP (12 mg, 0.1 mmol) and triethylamine (40 mg, 0.4 mmol) in dichloromethane (2 ml) was stirred overnight. The reaction mixture was purified by fresh chromatography over silica gel with 5% methanol in dichloromethane to give the title compound as a solid (27 mg 74% yield).

Workup

  1. customThe reaction mixture was purified by fresh chromatography over silica gel with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-012743d1f66d4eff873b8cb2180a9ad8
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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