Hydrochloric Acid → HCID 68680725, compound

HRID 2266857Notes

Reaction equation

HRID 2266857 reaction equation
FC(F)(F)C(O)=O.C[O:9][C:10]([C:12]1[O:13][C:14]([CH3:33])=[C:15]([CH2:17][NH:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][N:26]=3)=[CH:21][CH:20]=2)[CH:16]=1)=[O:11].[ClH:34]>O1CCCC1>[ClH:34].[CH3:32][O:31][C:28]1[CH:29]=[CH:30][C:25]([C:22]2[CH:21]=[CH:20][C:19]([NH:18][CH2:17][C:15]3[CH:16]=[C:12]([C:10]([OH:11])=[O:9])[O:13][C:14]=3[CH3:33])=[CH:24][CH:23]=2)=[N:26][CH:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68682297HCID 68682297, compound

Product 1

HCID 68680725HCID 68680725, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-{[4-(5-methoxy-pyridin-2-yl)-phenylamino]methyl}-5-methyl-furan-2-carboxylic acid methyl ester trifluoroacetic acid salt (165) (38 mg, 0.082 mmoles) in tetrahydrofuran (4 ml) was treated with potassium trimethylsilanoate (63 mg, 0.049 mmoles) and the mixture stirred at room temperature for 16 hours. The mixture was evaporated to dryness and pumped under high vacuum to remove silanol volatiles. The residue was purified by HPLC to afford a residue, which was dissolved in 1M aqueous hydrochloric acid. The solution was evaporated to give compound 166 as a solid (30 mg). LC/MS System A; Rt=2.22 mins, m/z (ES+)=339 (M+H for C19H18N2O4) and m/z (ES−)=337 (M−H for C26H25N3O5S).

Workup

  1. customThe mixture was evaporated to dryness
  2. customto remove silanol volatiles
  3. customThe residue was purified by HPLC
  4. customto afford a residue, which
  5. customThe solution was evaporated

Sources & evidence

ORD record
ord-c177181b888b4b008608f791e07b6b88
Source dataset
uspto-grants-2010_12
Patent number
US07858644B2

Reaction notes

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