Sodium Hydroxide → HCID 11646277, compound

HRID 2092148Notes

Reaction equation

HRID 2092148 reaction equation
COC([N:5]1[C:13]2[C:8](=[C:9]([NH:14][C:15]([NH:17][CH:18]3[C:27]4[C:22](=[CH:23][C:24]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:25][CH:26]=4)[O:21][CH2:20][CH2:19]3)=[O:16])[CH:10]=[CH:11][CH:12]=2)[CH:7]=[N:6]1)=O.[OH-].[Na+]>CO.O1CCCC1.O>[C:28]([C:24]1[CH:23]=[C:22]2[C:27]([CH:18]([NH:17][C:15]([NH:14][C:9]3[CH:10]=[CH:11][CH:12]=[C:13]4[C:8]=3[CH:7]=[N:6][NH:5]4)=[O:16])[CH2:19][CH2:20][O:21]2)=[CH:26][CH:25]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 67236455HCID 67236455, compound

Product 1

HCID 11646277HCID 11646277, compoundYield 86.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product of Example 1D (1.00 g, 2.37 mmol) in a mixture of 5 mL methanol and 5 mL tetrahydrofuran was treated with 5M sodium hydroxide (2 mL) in methanol, and stirred at ambient temperature for 90 minutes. The reaction mixture was diluted with water, and the resulting precipitate was collected by filtration to give 0.75 g of the title compound (86% yield). 1H NMR (300 MHz, DMSO-d6) δ 13.00 (broad s, 1H), 8.59 (s, 1H), 8.03 (s, 1H), 7.66 (d, J=7.5 Hz, 1H), 7.20 (m, 2H), 7.10-6.90 (m, 4H), 4.91 (m, 1H), 4.30-4.12 (m, 2H), 2.20-2.00 (m, 2H), 1.22 (s, 9H). MS (ESI) m/e 365 (M+H)+. Calc'd. For C17H16N4O2.1.0; H2O: C, 65.95; H, 6.85; N, 14.65. Found: C, 65.93, H, 6.69, N, 14.41.

Workup

  1. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-24e8af3bd7b9432eb5b399292884fe85
Source dataset
uspto-grants-2013_05
Patent number
US08440691B2

Reaction notes

Loading…