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

HRID 216224Notes

Reaction equation

HRID 216224 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[CH2:10][CH2:11][NH:12][C:13]1[N:18]=[C:17]([O:19][CH3:20])[N:16]=[C:15]([C:21]2[CH:22]=[C:23]([C:27]([CH3:32])([CH3:31])[C:28]([OH:30])=[O:29])[CH:24]=[CH:25][CH:26]=2)[CH:14]=1.[CH3:33]O>>[CH3:33][O:29][C:28](=[O:30])[C:27]([C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([C:15]2[CH:14]=[C:13]([NH:12][CH2:11][CH2:10][C:4]3[CH:5]=[CH:6][C:7]([Cl:9])=[CH:8][C:3]=3[Cl:2])[N:18]=[C:17]([O:19][CH3:20])[N:16]=2)[CH:22]=1)([CH3:32])[CH3:31]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11669780Pgd2-IN-1

Product 1

HCID 576361162-(3-{6-[2-(2,4-Dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-phenyl)-2-methyl-propionic acid methyl ester

Conditions

Temperature
65 °C

Procedure

Hydrochloric acid (81.46 μL, 4M solution in 1,4-dioxane, 0.33 mmol) is added to a stirred solution of 2-(3-{6-[2-(2,4-dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-phenyl)-2-methyl-propionic acid [100 mg, 0.22 mmol, Example 49(b)] in MeOH (8 mL), and the reaction mixture is stirred overnight at 65° C. The reaction is cooled to room temperature and concentrated in vacuo. The residue is purified by chromatography to afford 2-(3-{6-[2-(2,4-dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-phenyl)-2-methyl-propionic acid methyl ester (34 mg, Example 79). LCMS: RT=2.79 minutes; MS: 475 (M+H); 1H NMR (300 MHz, CDCl3): □7.98 (1H, s), 7.88 (1H, b), 7.42 (3H, d, J=2 Hz), 7.2 (2H, s), 6.4 (1H, s), 5.08 (1H, b), 4.05 (3H, s), 3.7 (2H, b), 3.65 (3H, s), 3.1 (2H, t, J=2 Hz), 1.65 (6H, s).

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-cb8dcbc39fdc4e9ea1041b693bd83cc2
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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