Hydrochloric Acid → N4-[2-(5-chloro-2-fluoro-phenyl)-[1,8]naphthyridin-4-yl]-pyrimidine-2,4-diamine

HRID 2409237Notes

Reaction equation

HRID 2409237 reaction equation
C(OC(=O)[NH:7][C:8]1[N:13]=[C:12]([NH:14][C:15]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[C:17]([C:25]3[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=3[F:32])[CH:16]=2)[CH:11]=[CH:10][N:9]=1)(C)(C)C.Cl>O1CCOCC1>[Cl:31][C:29]1[CH:28]=[CH:27][C:26]([F:32])=[C:25]([C:17]2[CH:16]=[C:15]([NH:14][C:12]3[CH:11]=[CH:10][N:9]=[C:8]([NH2:7])[N:13]=3)[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH:30]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53372717{4-[2-(5-Chloro-2-fluoro-phenyl)-[1,8]naphthyridin-4-ylamino]-pyrimidin-2-yl}-carbamic acid tert-butyl ester

Product 1

HCID 53372718N4-[2-(5-chloro-2-fluoro-phenyl)-[1,8]naphthyridin-4-yl]-pyrimidine-2,4-diamineYield 82.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

88 mg of {4-[2-(5-chloro-2-fluoro-phenyl)-[1,8]naphthyridin-4-ylamino]-pyrimidin-2-yl}-carbamic acid tert-butyl ester (cf. EXAMPLE 8a) were treated with 6 ml 4 m HCl in dioxane at ambient temperature for 4 hrs. After evaporation the product was digerated with ether and isolated by filtration to give 57 mg of N4-[2-(5-chloro-2-fluoro-phenyl)-[1,8]naphthyridin-4-yl]-pyrimidine-2,4-diamine as hydrochloride salt with Rt˜1.36 min and correct mass found M+H˜367.

Workup

  1. customAfter evaporation the product
  2. customisolated by filtration

Sources & evidence

ORD record
ord-54b62b2941c14ca79a01541d3025a096
Source dataset
uspto-grants-2014_08
Patent number
US08815893B2

Reaction notes

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