Hydrochloric Acid → HCID 10371276, compound

HRID 1296976Notes

Reaction equation

HRID 1296976 reaction equation
[Cl:1][C:2]1[C:36]([C:37]([F:40])([F:39])[F:38])=[CH:35][CH:34]=[CH:33][C:3]=1[CH2:4][N:5]([CH2:19][CH:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=1.[CH3:41][N:42]([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)[CH3:43].F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.Cl>C(#N)C.CS(C)=O>[Cl:1][C:2]1[C:36]([C:37]([F:40])([F:39])[F:38])=[CH:35][CH:34]=[CH:33][C:3]=1[CH2:4][N:5]([CH2:19][CH:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([N:42]([CH3:43])[CH3:41])=[O:15])=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 69414852HCID 69414852, compound

Product 1

HCID 10371276HCID 10371276, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 4-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-benzoic acid (0.023 g, 0.041 mmol) in acetonitrile (3 ml) was treated with BOP reagent (0.02 g, 0.04 mmol) followed by triethylamine (0.013 mL, 0.09 mmol). To the mixture was added (CH3)2NH2.HCl (4 mg, 0.045 mmol), and the reaction was stirred at ambient temperature overnight. The reaction mixture was then concentrated in-vacuo to afford an oil. The crude product was then dissolved in DMSO and purified via reverse-phase HPLC (TMC CombiPrep PDS, 75×30 mm, 25 mL/min, acetonitrile:H2O, UV detection at 254 nm) to afford the title compound, 186 mg (77%); MS (ESI) m/e 596 [M+H]+.

Workup

  1. concentrationThe reaction mixture was then concentrated in-vacuo
  2. customto afford an oil
  3. custompurified via reverse-phase HPLC (TMC CombiPrep PDS, 75×30 mm, 25 mL/min, acetonitrile:H2O, UV detection at 254 nm)

Sources & evidence

ORD record
ord-c222385637bd45bfa2ae27e1e8b3f2bd
Source dataset
uspto-grants-2007_07
Patent number
US07247748B2

Reaction notes

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