3-Bromo-1-propanol → 4-{6-(3-[(2-Chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-amino]-propoxy}-pyridin-2-yl)-piperazine-1-carboxylic Acid Tert-Butyl Ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:21]1([CH:27]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH2:28][N:29]([CH2:42][CH2:43][CH2:44]O)[CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[C:32]=2[Cl:41])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.OC1C=C(C=CC=1)CC1N(COCC)N=NN=1.BrCCCO>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:44][CH2:43][CH2:42][N:29]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:38])([F:39])[F:40])[C:32]=3[Cl:41])[CH2:28][CH:27]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
5
Reactant 4
Product 1
Procedure
Following the procedure of Example 6(d), except 4-(6-Hydroxy-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester and N-(2,2-Diphenylethyl)-N-(3-hydroxy-propyl)-N-(2-chloro-3-trifluoromethyl-benzyl)amine were used instead of 5-(3-hydroxy-benzyl)-ethoxymethyl-1,2,3,4-tetrazole and 3-bromo-propanol in step 6(d), the title compound was synthesized as the free base, 0.46 g (52% yield), as a white solid. MS (ESI) 709.4 (M+).
Sources & evidence
- ORD record
- ord-2ed529e330d34dd4aaa3f1bc3881e715
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07365085B2
Reaction notes
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