HCID 10281380, compound → HCID 10162111, compound

HRID 971114Notes

Reaction equation

HRID 971114 reaction equation
[CH:1]([NH:4][C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([N:30]4[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]4)=[CH:26][CH:25]=3)[CH:19]=2)[CH:8]=1)=[O:6])([CH3:3])[CH3:2]>C(Cl)Cl>[CH:1]([NH:4][C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([N:30]4[CH2:31][CH2:32][NH:33][CH2:34][CH2:35]4)=[CH:26][CH:25]=3)[CH:19]=2)[CH:8]=1)=[O:6])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 10281380HCID 10281380, compound

Product 1

HCID 10162111HCID 10162111, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-isopropyl-1-{3-[4-(4-tertbutyloxycarbonylpiperazin-1-yl)phenyl]-phenyl}-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide from Example 11 in methylene chloride (10 ml/mmol) was added trifluororacetic acid (6 ml/mmol) and the resulting mixture was stirred at room temperature for 2 hours, then warmed gently for 15 minutes. The mixture was evaporated and the crude product was chromatographed on silica gel eluting with a 9:0.9:0.1 mixture of methylene chloride, methanol and 28% aqueous ammonium hydroxide to afford the title compound as a solid.

Workup

  1. temperaturewarmed gently for 15 minutes
  2. customThe mixture was evaporated
  3. customthe crude product was chromatographed on silica gel eluting with a 9:0.9:0.1 mixture of methylene chloride, methanol and 28% aqueous ammonium hydroxide

Sources & evidence

ORD record
ord-2b9a6c87d9d74b10898b562c2e71e5a8
Source dataset
uspto-grants-2007_12
Patent number
US07312334B2

Reaction notes

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