Sodium Hydroxide → HCID 11646277, compound

HRID 1158788Notes

Reaction equation

HRID 1158788 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-cb6c349b8c7544ce96239e59936f7b4e
Source dataset
uspto-grants-2010_10
Patent number
US07812019B2

Reaction notes

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