Sodium Hydroxide → HCID 66746897, compound

HRID 1467243Notes

Reaction equation

HRID 1467243 reaction equation
[C:1]([C:3]1[C:8]([O:9][CH2:10][C:11]([CH3:19])([CH3:18])[C:12](=[O:17])[NH:13][CH2:14][CH2:15][CH3:16])=[CH:7][CH:6]=[CH:5][C:4]=1[NH:20][C:21]([NH:23]C(=O)C1C=CC=CC=1)=[O:22])#[N:2].[OH-].[Na+]>CCO>[NH2:2][C:1]1[C:3]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:9][CH2:10][C:11]([CH3:19])([CH3:18])[C:12]([NH:13][CH2:14][CH2:15][CH3:16])=[O:17])[NH:20][C:21](=[O:22])[N:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66745827HCID 66745827, compound

Product 1

HCID 66746897HCID 66746897, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(2-cyano-3-(2,2-dimethyl-3-oxo-3-(propylamino)propoxy)-phenylcarbamoyl)benzamide (example 203a) (141 mg, 0.3 mmol) and NaOH (2 N, 0.3 mL) in EtOH (5 mL) was stirred at 100° C. under nitrogen for 2 hrs. After cooling to room temperature, the clear reaction solution was filtered, and the filtrate was carefully neutralized with 10% AcOH with vigorous stirring at 0° C. The resultant precipitate was collected by filtration, washed with water and then 20% EtOH in water to give the final product (81 mg) in 76% yield as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 0.73 (t, J=7.4 Hz, 3H), 1.21 (s, 6H), 1.33-1.41 (m, 2H), 3.01 (q, J=7.4 Hz, 2H), 4.08 (s, 2H), 6.64 (d, J=8.0 Hz, 1H), 6.69 (d, J=8.0 Hz, 1H), 7.42 (t, J=8.0 Hz, 1H), 7.47 (s, 1H), 7.79 (t, J=7.4 Hz, 1H), 7.84 (s, 1H), 10.60 (s, 1H). MS 319 (MH+).

Workup

  1. filtrationthe clear reaction solution was filtered
  2. filtrationThe resultant precipitate was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-40ca0f47cb074ffc9c8c06f1e69130ee
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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