Methanesulfonic Acid → (2-Chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-{3-[6-(4-methyl-piperazin-1-yl)-pyridin-2-yloxy]-propyl}-amine dimesylate salt

HRID 902651Notes

Reaction equation

HRID 902651 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[C:12]([OH:14])[CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[C:15]1([CH:21]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:22][N:23]([CH2:36][CH2:37][CH2:38]O)[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[C:26]=2[Cl:35])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.OC1C=C(C=CC=1)CC1N(COCC)N=NN=1.BrCCCO.[CH3:68][S:69]([OH:72])(=[O:71])=[O:70]>ClCCl>[S:69]([OH:72])(=[O:71])(=[O:70])[CH3:68].[S:69]([OH:72])(=[O:71])(=[O:70])[CH3:68].[Cl:35][C:26]1[C:27]([C:31]([F:32])([F:33])[F:34])=[CH:28][CH:29]=[CH:30][C:25]=1[CH2:24][N:23]([CH2:22][CH:21]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:36][CH2:37][CH2:38][O:14][C:12]1[CH:11]=[CH:10][CH:9]=[C:8]([N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)[N:13]=1

Participants

7

Reactant 5

HCID 6395Methanesulfonic AcidHCID 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 178480672HCID 178480672, compound

Product 1

HCID 86598286(2-Chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-{3-[6-(4-methyl-piperazin-1-yl)-pyridin-2-yloxy]-propyl}-amine dimesylate salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure of Example 6(d), except 6-(4-methyl-piperazin-1-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 dichloromethane and two equivalents of methanesulfonic acid were added to afford the title compound as the dimesylate salt, 47 mg (19% yield), as a white solid. MS (ESI) 623.4 (M+).

Workup

  1. customthe title compound was synthesized as the free base

Sources & evidence

ORD record
ord-69d7d342c37b44f9a7e3b40a2974405e
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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