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Sodium Hydroxide → 5-(4-(2-(5-Amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)phenoxy)pentanoic acid

HRID 340357
Notes
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Reaction equation

HRID 340357 reaction equation
[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8]([CH2:12][CH2:13][C:14]3[CH:29]=[CH:28][C:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25]CC)=[O:24])=[CH:16][CH:15]=3)=[CH:7][C:6]=2[C:5]2[CH:30]=[CH:31][C:32]([CH3:34])=[CH:33][C:4]=2[N:3]=1.[OH-].[Na+]>C(O)C.C(OCC)(=O)C.O>[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8]([CH2:12][CH2:13][C:14]3[CH:29]=[CH:28][C:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:16][CH:15]=3)=[CH:7][C:6]=2[C:5]2[CH:30]=[CH:31][C:32]([CH3:34])=[CH:33][C:4]=2[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 58213647Ethyl 5-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)phenoxy)pentanoate

Product 1

HCID 582137705-(4-(2-(5-Amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)phenoxy)pentanoic acid

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 5-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)phenoxy)pentanoate (1.0 equiv.) (from Example 139) in ethanol (0.10 M) was added anhydrous sodium hydroxide (2.0 equiv.) and the resulting mixture was allowed to stir at 80° C. for 2 hours. After cooling to ambient temperature, the mixture was diluted with ethyl acetate and water. The biphasic layers were separated and the aqueous layer was washed twice with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4 and the volatiles were removed in vacuo. The resulting residue was purified by a COMBIFLASH® system (ISCO) using 0-10% methanol in dichloromethane to furnish 5-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)phenoxy)pentanoic acid as a solid. 1H NMR (Methanol-d4): δ 8.61 (s, 1H), 8.57 (s, 1H), 8.20 (d, 1H), 7.40 (s, 1H), 7.20 (d, 1H), 7.07 (d, 2H), 6.81 (d, 2H), 3.93 (t, 2H), 3.18 (t, 2H), 3.00 (t, 2H), 2.48 (s, 3H), 2.25 (t, 2H), 1.74-1.81 (m, 2H), 0.86-0.96 (m, 2H). LRMS [M+H]=430.2

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customThe biphasic layers were separated
  3. washthe aqueous layer was washed twice with ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. customthe volatiles were removed in vacuo
  6. customThe resulting residue was purified by a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-3e6a1619f23c42329ddf1502a1e0af36
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08895577B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes