Hydrochloric Acid → HCID 69069405, compound

HRID 216117Notes

Reaction equation

HRID 216117 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[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>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[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

6

Reactant 2

HCID 313Hydrochloric AcidHCID 57636021HCID 57636021, compound

Product 1

HCID 69069405HCID 69069405, compoundYield 152.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-{6-[2-(2-chloro-6-fluoro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-benzoic acid [0.1 g, Example 20(b)] in DCM and MeOH is treated with a saturated solution of hydrogen chloride in EtOAc (2 mL) and the mixture is concentrated, dissolved in acetonitrile and water, and lyophilized to afford 3-{6-[2-(2-chloro-6-fluoro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-benzoic acid hydrochloride [83 mg, Example 15(c)] as a solid. LCMS: RT=2.85 minutes, MS: 402 (M+H).

Workup

  1. concentrationthe mixture is concentrated
  2. dissolutiondissolved in acetonitrile

Sources & evidence

ORD record
ord-925500de924c4eea946db71242282a69
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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