N,N-Dimethyl-1,3-propanediamine → 4'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl4-carboxylic acid (3-dimethylamino-propyl)-amide
Reaction equation
[O:1]([CH2:8][CH2:9][S:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([OH:26])=O)=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:39][N:40]([CH3:45])[CH2:41][CH2:42][CH2:43][NH2:44]>C1COCC1>[CH3:39][N:40]([CH3:45])[CH2:41][CH2:42][CH2:43][NH:44][C:24]([C:21]1[CH:20]=[CH:19][C:18]([C:15]2[CH:14]=[CH:13][C:12]([CH2:11][S:10][CH2:9][CH2:8][O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:17][CH:16]=2)=[CH:23][CH:22]=1)=[O:26]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
4′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (3-dimethylamino-propyl)-amide was prepared as described in example 1. 4′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (0.6 g, 1.65 mmol, 1 eq.) in THF was treated with 1,1′-carbonyldiimidazole (0.27 g, 1.68 mmol, 1.02 eq.). The resulting acyl imidazole was then treated with 3-(dimethylamino)propylamine (0.20 g, 1.98 mmol, 1.2 eq.). When complete, the reaction was worked up and the resulting yellow oil purified as described in example 3 to give 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl4-carboxylic acid (3-dimethylamino-propyl)-amide (0.55 g, 74% yield) as a white solid.
Workup
- custom4′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (3-dimethylamino-propyl)-amide was prepared
- customthe resulting yellow oil purified
Sources & evidence
- ORD record
- ord-7373074a7d59463899c3e96706d2a06f
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07132456B2
Reaction notes
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