Hydrochloric Acid → 2-(3-{6-[2-(2,4-Dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-phenyl)-2-methyl-propionic acid hydrochloride

HRID 216118Notes

Reaction equation

HRID 216118 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][NH:11][C:12]1[N:17]=[C:16]([O:18][CH3:19])[N:15]=[C:14]([C:20]2[CH:21]=[C:22]([C:26]([CH3:31])([CH3:30])[C:27]([OH:29])=[O:28])[CH:23]=[CH:24][CH:25]=2)[CH:13]=1.Cl>CO.CCOCC>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][NH:11][C:12]1[N:17]=[C:16]([O:18][CH3:19])[N:15]=[C:14]([C:20]2[CH:21]=[C:22]([C:26]([CH3:31])([CH3:30])[C:27]([OH:29])=[O:28])[CH:23]=[CH:24][CH:25]=2)[CH:13]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11669780Pgd2-IN-1

Product 1

HCID 690688762-(3-{6-[2-(2,4-Dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-phenyl)-2-methyl-propionic acid hydrochlorideYield 174.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-(3-{6-[2-(2,4-dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-phenyl)-2-methyl-propionic acid [4.3 g, 9.35 mmol, Example 49(b)] in MeOH is treated with 1 M hydrogen chloride in ether (18 mL). The mixture is evaporated and the resulting oil is dissolved in acetone (10 mL). After 2 minutes a solid precipitated. This is filtered giving 2-(3-{6-[2-(2,4-Dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-phenyl)-2-methyl-propionic acid hydrochloride [4.043 g, 87%, Example 15(d)] as a solid. LC/MS: RT=2.42 minutes, MS: 460 (M+H). 1H NMR [(CD3)2SO]: □ 12.4 (1H, br s), 7.36-7.8 (7H, m), 6.6 (1H, s), 4 (3H, s), 3.7 (2H, m), 3.02 (2H, m), 1.54 (6H, s). IC50=0.3 nM

Workup

  1. customThe mixture is evaporated
  2. dissolutionthe resulting oil is dissolved in acetone (10 mL)
  3. customAfter 2 minutes a solid precipitated
  4. filtrationThis is filtered

Sources & evidence

ORD record
ord-71f52ebe89ba4df3916862302135eb1d
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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