N,N-Dimethyl-1,3-propanediamine → HCID 86755126, compound

HRID 377372Notes

Reaction equation

HRID 377372 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](/[CH:10]=[CH:11]/[CH:12]=[C:13](\[O:17][CH3:18])/[C:14]([OH:16])=O)=[CH:7][C:6]=2[CH:19]=1.CN(C)[CH2:22][CH2:23]CN.O.ON1[C:33]2[N:34]=[CH:35][CH:36]=[CH:37][C:32]=2N=N1.Cl.C[N:40](C)CCCN=C=NCC>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](/[CH:10]=[CH:11]/[CH:12]=[C:13](\[O:17][CH3:18])/[C:14]([NH:40][CH2:37][CH2:36][CH2:35][N:34]([CH2:33][CH3:32])[CH2:22][CH3:23])=[O:16])=[CH:7][C:6]=2[CH:19]=1

Participants

6

Reactant 4

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19358675HCID 19358675, compoundHCID 219174661-Hydroxy-7-azabenzotriazol hydrate

Product 1

HCID 86755126HCID 86755126, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (2Z,4E)-5-(5-chlorobenzofuran-2-yl)-2-methoxy-2,4-pentadienoic acid (88 mg, 0.32 mmol), 3-dimethylamino propylamine (46 mg, 0.35 mmol), 1-hydroxy-7-azabenzotriazole hydrate (44 mg, 0.32 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (62 mg, 0.5 mmol) in DMF (2 ml) was stirred at RT for 6 hours. After the same work up as seen in example 3 pure title compound was obtained (60 mg, 0.153 mmol, yield 48.0%) as yellow crystals, mp.=150° dec.

Sources & evidence

ORD record
ord-b6609cda7ef641f7b067d160056b93f2
Source dataset
uspto-grants-2000_02
Patent number
US06025390

Reaction notes

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