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

HRID 2110643Notes

Reaction equation

HRID 2110643 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]([CH:26]=[CH:27][CH:28]=2)[C:23]([OH:25])=[O:24])[CH:13]=1.Cl>C(Cl)Cl.CO.CCOC(C)=O.C(#N)C.O.Cl>[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]([CH:26]=[CH:27][CH:28]=2)[C:23]([OH:25])=[O:24])[CH:13]=1

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 533205273-{6-[2-(2,4-Dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-benzoic acid

Product 1

HCID 690729463-{6-[2-(2,4-Dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-benzoic acid hydrochlorideYield 158.2%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 86615699Acetonitrile-hcl-waterSolvent

Procedure

A suspension of 3-{6-[2-(2,4-dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-benzoic acid [0.2 g, Example 35(w)] in DCM and MeOH is treated with a saturated solution of hydrogen chloride in EtOAc (0.5 mL), and chromatographed on silica gel eluting with 10% MeOH in DCM to provide the product, which is dissolved in acetonitrile/water/hydrochloric acid, and lyophilized to give 3-{6-[2-(2,4-dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-benzoic acid hydrochloride [172 mg, Example 15(b)] as a solid. LCMS: RT=2.72 minutes, MS: 417 (M+H).

Workup

  1. customchromatographed on silica gel eluting with 10% MeOH in DCM
  2. customto provide the product, which

Sources & evidence

ORD record
ord-55035ef1b56448428b550bcd8c415b16
Source dataset
uspto-grants-2009_04
Patent number
US07517889B2

Reaction notes

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