2-Methoxybenzylamine → HCID 86754318, compound

HRID 583396Notes

Reaction equation

HRID 583396 reaction equation
[CH3:1][N:2]([CH:19]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[CH:20]=[CH:21][C:22]([OH:24])=O)[C:3](=[O:18])[C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([C:14]([F:17])([F:16])[F:15])[CH:5]=1.[CH3:33][O:34][C:35]1[CH:42]=[CH:41][CH:40]=[CH:39][C:36]=1[CH2:37][NH2:38].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:33][O:34][C:35]1[CH:42]=[CH:41][CH:40]=[CH:39][C:36]=1[CH2:37][NH:38][C:22](=[O:24])[CH:21]=[CH:20][CH:19]([N:2]([CH3:1])[C:3](=[O:18])[C:4]1[CH:5]=[C:6]([C:14]([F:15])([F:17])[F:16])[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1)[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 812922-MethoxybenzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53723640HCID 53723640, compound

Product 1

HCID 86754318HCID 86754318, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

This is the compound of Example 1. It can be prepared also by the following synthesis method: a mixture of 0.493 g of 4-[N'-methyl-N'-(3,5-bistrifluoromethyl-benzoyl)-amino]-5-(4-chlorophenyl)-pent-2-enoic acid, 0.137 g of 2-methoxy-benzylamine, 0.21 g of N-ethyl-N'-(3-dimethylaminopropyl)-carbodiimide hydrochloride, 0.134 g of 4-dimethylaminopyridine and 10 ml of methylene chloride is stirred at room temperature under argon for 16 hours and then concentrated by evaporation. The residue is chromatographed (silica gel, hexane/ethyl acetate 1:1). In this way the title compound is obtained in the form of a colourless amorphous solid. 1H-NMR, 200 MHz, CDCl3, delta (ppm): 7.3-7.0(m, 4H), 6.95-6.7(m, 5H), 6.0(s,1H), 5.77(d, 1H), 5.0(b, 1H), 4.5(d, 2H), 3.85(s, 3H), 2.9-2.6(m, 5H), 1.3(bs, 9H).

Workup

  1. customIt can be prepared also by the following synthesis method
  2. concentrationconcentrated by evaporation
  3. customThe residue is chromatographed (silica gel, hexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-99dd9644ba054497a81ab5161173f631
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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