Benzylamine → 1-{4'-[4-(2-Benzylamino-1-hydroxy-ethyl)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester

HRID 1183316Notes

Reaction equation

HRID 1183316 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH:27]4[CH2:29][O:28]4)=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH2:30]([NH2:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CN1CCCC1>>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH:27]([OH:28])[CH2:29][NH:37][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:7][CH2:8]1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 7504Benzylamine2×HCID 84541-MethylpyrrolidineHCID 866524031-[4'-(3-Methyl-4-oxiranyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 665773521-{4'-[4-(2-Benzylamino-1-hydroxy-ethyl)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester

Conditions

Temperature
85 °C

Procedure

1-[4′-(3-Methyl-4-oxiranyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (0.100 g, 0.26 mmol), benzylamine (0.034 mL, 0.31 mmol) and N-methylpyrrolidine (5 mL) were combined in a flask and stirred at 85° C. overnight. An additional portion of benzylamine (0.050 mL) was added and the reaction continued to stir at 85° C. for 48 hours. The reaction mixture was cooled and submitted to standard aqueous workup to give the title compound.

Workup

  1. stirringto stir at 85° C. for 48 hours
  2. temperatureThe reaction mixture was cooled

Sources & evidence

ORD record
ord-b65498b6e1da43818fea41fa468f5aa1
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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