Acetic Acid → HCID 56847104, compound

HRID 1847620Notes

Reaction equation

HRID 1847620 reaction equation
[CH2:1]([NH:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[N:17]=[C:16]([C:21](OC)=[O:22])[CH:15]=[CH:14][C:13]=2[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K].[NH2:26][OH:27].C(O)(=O)C>CO>[CH2:1]([NH:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[N:17]=[C:16]([C:21]([NH:26][OH:27])=[O:22])[CH:15]=[CH:14][C:13]=2[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 66778751HCID 66778751, compoundHCID 86662665HCID 86662665, compound

Product 1

HCID 56847104HCID 56847104, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a vial containing methyl 6-(benzylcarbamoyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-2-carboxylate was added MeOH (1 mL) and hydroxylamine potassium salt (1 mL, 1.76 mmol, 1.76 M in MeOH) and the resulting mixture was shaken at rt for 13 h. The solution was quenched with acetic acid (0.200 mL, 3.52 mmol) before being concentrated. To the resulting residue was added DMSO (1.2 mL) and it was purified via prep-HPLC to yield N6-benzyl-N2-hydroxy-7,8-dihydro-1,6-naphthyridine-2,6(5H)-dicarboxamide (0.0113 g, 36.0%). LC-MS: (FA) ES+ 327; 1H NMR (Methanol-d4, 400 MHz) δ 7.86 (d, J=7.8 Hz, 1 H), 7.70 (d, J=8.0 Hz, 1 H), 7.25-7.19 (m, 5 H), 4.68 (s, 2 H), 4.39 (s, 2 H), 3.79 (t, J=6.0 Hz, 2 H), 3.03 (t, J=6.0 Hz, 2 H).

Workup

  1. concentrationbefore being concentrated
  2. additionTo the resulting residue was added DMSO (1.2 mL) and it
  3. customwas purified via prep-HPLC

Sources & evidence

ORD record
ord-495c960f729b4f459f797591877951e6
Source dataset
uspto-grants-2015_02
Patent number
US08952163B2

Reaction notes

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