Sodium Hydroxide → HCID 69193072, compound

HRID 1187402Notes

Reaction equation

HRID 1187402 reaction equation
Cl.C([O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][NH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][N:20]=2)[N:15]=[CH:14][C:13]=1[NH:22][C:23](=O)[CH2:24][CH2:25][CH3:26])(=O)C.[OH-].[Na+]>C(O)C>[CH2:24]([C:23]1[N:11]([CH2:10][CH2:9][O:8][CH2:7][CH2:6][OH:5])[C:12]2[C:21]3[N:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:22]=1)[CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 69180653HCID 69180653, compound

Product 1

HCID 69193072HCID 69193072, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Modifying the procedure described in Part E of Examples 127-135, 2-(2-{[3-(butyrylamino)[1,5]naphthyridin-4-yl]amino}ethoxy)ethyl acetate hydrochloride (approximately 24.5 mmol) was treated with 2 M NaOH (37 mL, 73.5 mmol) in ethanol. After the solution was heated at 60° C. overnight, more 2 M NaOH was added (1 equivalent) and the mixture was heated at 70° C. for 8 hours. After the work-up described in Part E of Examples 127-135, 6.55 g of 2-[2-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethoxy]ethanol was isolated as an orange solid.

Workup

  1. temperaturethe mixture was heated at 70° C. for 8 hours

Sources & evidence

ORD record
ord-bb53bec4db1f46f4b9f018a26bbe52db
Source dataset
uspto-grants-2014_03
Patent number
US08673932B2

Reaction notes

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