Ethanol → HCID 58379645, compound

HRID 1630353Notes

Reaction equation

HRID 1630353 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:28]4[CH:29]=[N:30][C:31]5[C:36]([CH:37]=4)=[CH:35][CH:34]=[CH:33][CH:32]=5)[N:26]=3)[N:21]=[CH:20][C:19]=2[C:38]([O:40]C)=[O:39])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+].C(O)C>O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:28]4[CH:29]=[N:30][C:31]5[C:36]([CH:37]=4)=[CH:35][CH:34]=[CH:33][CH:32]=5)[N:26]=3)[N:21]=[CH:20][C:19]=2[C:38]([OH:40])=[O:39])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 67345240HCID 67345240, compound

Product 1

HCID 58379645HCID 58379645, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of compound 46 (8.2 g, 15 mmol) and lithium hydroxide (480 mg, 20 mmol) in 2:1 ethanol:water (150 mL) was heated to 75° C. resulting in a solution. After 2 hours, the solution was cooled to room temperature and concentrated. The residue was taken up in water (200 mL) and the solution was acidified with 1 N HCl (20 mL). The precipitate was collected by filtration and dried at 60° C. under vacuum to afford 4-({1-[(benzyloxy)carbonyl]piperidin-4-yl}amino)-6-quinolin-3-yl-1,5-naphthyridine-3-carboxylic acid (compound 47) (7.8 g, 98%).

Workup

  1. customresulting in a solution
  2. concentrationconcentrated
  3. filtrationThe precipitate was collected by filtration
  4. customdried at 60° C. under vacuum

Sources & evidence

ORD record
ord-9fe26da7f04446ec9d9e65e2db7639fc
Source dataset
uspto-grants-2014_07
Patent number
US08791131B2

Reaction notes

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