3-Bromo-1-propanol → (2-Chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-[3-(6-morpholin-4-yl-pyridin-2-yloxy)-propyl]-amine hydrochloride salt

HRID 902648Notes

Reaction equation

HRID 902648 reaction equation
[N:1]1([C:7]2[N:12]=[C:11]([OH:13])[CH:10]=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:14]1([CH:20]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:21][N:22]([CH2:35][CH2:36][CH2:37]O)[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[C:25]=2[Cl:34])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.OC1C=C(C=CC=1)CC1N(COCC)N=NN=1.BrCCCO>C(OCC)C>[ClH:34].[Cl:34][C:25]1[C:26]([C:30]([F:31])([F:32])[F:33])=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][N:22]([CH2:21][CH:20]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:35][CH2:36][CH2:37][O:13][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]([N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)[N:12]=1

Participants

6

Reactant 4

HCID 123083-Bromo-1-propanolHCID 577571173-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-olHCID 688254685-(3-Hydroxy-benzyl)-ethoxymethyl-1,2,3,4-tetrazoleHCID 178516081HCID 178516081, compound

Product 1

HCID 69253588(2-Chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-[3-(6-morpholin-4-yl-pyridin-2-yloxy)-propyl]-amine hydrochloride saltYield 32%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Following the procedure of Example 6(d), except 6-morpholin-4-yl-pyridin-2-ol 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. The tertiaryamine was then dissolved in diethyl ether and acidified with 1.0 M HC/diethyl ether to give 90 mg (32% yield) of the title compound as a white solid. MS (ESI) 610.2 (M+).

Workup

  1. customthe title compound was synthesized as the free base

Sources & evidence

ORD record
ord-83f2a593dbca4e58881708fed225c2f6
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

Loading…