Water → HCID 86670482, compound

HRID 68974Notes

Reaction equation

HRID 68974 reaction equation
[H-].[Na+].[CH2:3]([N:5]1[C:11](=[O:12])[C:10]([CH3:14])([CH3:13])[C:9](=[O:15])[N:8]([CH3:16])[C:7]2[CH:17]=[C:18]([CH2:21][N:22]([CH2:35][CH2:36][C:37]3[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=3)[C:23](=[O:34])CC3C4C(=CC=CC=4)NN=3)[CH:19]=[CH:20][C:6]1=2)[CH3:4].CI.O>CN(C=O)C>[CH2:3]([N:5]1[C:11](=[O:12])[C:10]([CH3:14])([CH3:13])[C:9](=[O:15])[N:8]([CH3:16])[C:7]2[CH:17]=[C:18]([CH2:21][N:22]([CH2:35][CH2:36][C:37]3[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=3)[CH:23]=[O:34])[CH:19]=[CH:20][C:6]1=2)[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178462947HCID 178462947, compound

Product 1

HCID 86670482HCID 86670482, compoundYield 10.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (55% in oil) (52 mg) was suspended in DMF (7 ml), and cooled to 0° C. in an ice water bath. N-(1-Ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-ylmethyl)-2-(1H-indazol-3-yl)-N-(2-pyridin-3-ylethyl)acetamide (210 mg) was added thereto at the same temperature, and the mixture was stirred at 0° C. for 30 minutes followed at room temperature for 30 minutes. Methyl iodide (0.03 ml) was added thereto, and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction liquid, followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate, and condensed under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=85:15). The purified product was condensed to dryness to give the title compound (17 mg) as a pale yellow white amorphous.

Workup

  1. waitfollowed at room temperature for 30 minutes
  2. stirringthe mixture was stirred at room temperature for 3 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate, and condensed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=85:15)
  6. customcondensed to dryness

Sources & evidence

ORD record
ord-6f9016c868a54e698abcb02ab6c1643f
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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