Triethylamine → [2-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-ethyl]-pyrimidin-2-yl-amine hydrochloride salt

HRID 902697Notes

Reaction equation

HRID 902697 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:38]=[CH:39][CH:40]=1)[O:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[C:28]=1[Cl:37])[CH2:12][CH:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl[C:42]1[N:47]=[CH:46][CH:45]=[CH:44][N:43]=1.C(N(CC)CC)C>C(O)C>[ClH:37].[Cl:37][C:28]1[C:29]([C:33]([F:34])([F:35])[F:36])=[CH:30][CH:31]=[CH:32][C:27]=1[CH2:26][N:11]([CH2:12][CH:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:10][CH2:9][CH2:8][O:7][C:6]1[CH:5]=[C:4]([CH2:3][CH2:2][NH:1][C:42]2[N:47]=[CH:46][CH:45]=[CH:44][N:43]=2)[CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 744042-ChloropyrimidineHCID 59701396HCID 59701396, compound

Product 1

HCID 69252291[2-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-ethyl]-pyrimidin-2-yl-amine hydrochloride salt

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring solution of {3-[3-(2-amino-ethyl)-phenoxy]-propyl}-(2-chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-amine (57 mg, 0.1 mml, Example 150) and 2-Chloro-pyrimidine (97 mg, 0.85 mmol) in ethanol (10 mL) was added triethylamine (0.5 ml, 3.75 mmol). The resulting solution was refluxed for 72 hours and then concentrated in vacuo. Purification by preparative HPLC (YMC 75×30 mm, 25 m/min, 95-100% CH3CN) afforded the desired pyrimidine product. The free base was treated with 1 M HCl in Et2O (0.1 ml) and the mixture was concentrated in vacuo to afford the title compound as a solid, 44 mg (64%). MS(ES) m/e 645.4 (M+).

Workup

  1. temperatureThe resulting solution was refluxed for 72 hours
  2. concentrationconcentrated in vacuo
  3. customPurification by preparative HPLC (YMC 75×30 mm, 25 m/min, 95-100% CH3CN)

Sources & evidence

ORD record
ord-19579e3047e24962b0006bdb59b13099
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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