Water → HCID 135847203, compound

HRID 345765Notes

Reaction equation

HRID 345765 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:11]1[CH:16]=[C:15]([NH:17][C:18]2[CH:23]=[N:22][C:21]([C:24](OC)=[O:25])=[CH:20][N:19]=2)[CH:14]=[C:13]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:12]=1[OH:32])([CH3:10])([CH3:9])[CH3:8].O.S([O-])([O-])(=O)=O.[Mg+2]>C(OCC)C.O1CCCC1>[C:7]([C:11]1[CH:16]=[C:15]([NH:17][C:18]2[CH:23]=[N:22][C:21]([CH2:24][OH:25])=[CH:20][N:19]=2)[CH:14]=[C:13]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:12]=1[OH:32])([CH3:10])([CH3:9])[CH3:8]

Participants

7

Reactant 4

HCID 962WaterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 136094458HCID 136094458, compound2×

Product 1

HCID 135847203HCID 135847203, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (0.14 g) was suspended in 26 ml of diethyl ether. While the suspension was stirred at room temperature, 13 ml of a solution of 0.50 g of 2,6-di-tert-butyl-4-[(5-methoxycarbonyl-2-pyrazinyl)-amino]phenol (Compound 20) in tetrahydrofuran was added thereto. The resulting mixture was further stirred at room temperature for 4 hours. With cooling on an ice bath 0.5 ml of water was added thereto, followed by addition of 1.4 g of magnesium sulfate, and the mixture was stirred for 15 minutes. Insoluble materials were filtered off, and the filtrate was concentrated. The resulting crude product was purified by silica gel column chromatography (eluent: methanol-chloroform=1:19), giving 0.30 g of the title compound (Compound 32) as a pale yellow solid.

Workup

  1. stirringThe resulting mixture was further stirred at room temperature for 4 hours
  2. additionwas added
  3. stirringthe mixture was stirred for 15 minutes
  4. filtrationInsoluble materials were filtered off
  5. concentrationthe filtrate was concentrated
  6. customThe resulting crude product was purified by silica gel column chromatography (eluent: methanol-chloroform=1:19)

Sources & evidence

ORD record
ord-824aed9c80bf4f0285d5f086e74ebe96
Source dataset
uspto-grants-1991_10
Patent number
US05059598

Reaction notes

Loading…