Sodium hydride → HCID 69158211, compound

HRID 1394175Notes

Reaction equation

HRID 1394175 reaction equation
[NH2:1][C:2]1[C:3]([C:7]2[N:8]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)[C:9]3[CH:14]=[CH:13][N:12]=[CH:11][C:10]=3[N:15]=2)=[N:4][O:5][N:6]=1.[H-].[Na+].Cl.[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29][Cl:30]>CN(C)C=O>[ClH:30].[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29][O:22][C:19]1[CH:20]=[CH:21][C:16]([N:8]2[C:9]3[CH:14]=[CH:13][N:12]=[CH:11][C:10]=3[N:15]=[C:7]2[C:3]2[C:2]([NH2:1])=[N:6][O:5][N:4]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 57721189HCID 57721189, compound

Product 1

HCID 69158211HCID 69158211, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the product of Example 38 (30 mg, 0.102 mmol), in N,N-dimethylformamide (2 ml), was added sodium hydride (60% dispersion in mineral oil, 4 mg, 0.10 mmol). After 5 minutes at room temperature 2-(dimethylamino)ethyl chloride hydrochloride (15 mg, 0.102 mmol) and sodium hydride (60% dispersion in mineral oil, 4 mg, 0.102 mmol) were added and the reaction heated at 60° C. for 5 hours. The solvent was evaporated in vacuo and the residue was partitioned between ethyl acetate and 2M sodium hydroxide solution. The organic phase was separated then washed with water (×3), dried over anhydrous sodium sulphate and evaporated in vacuo. Purification of the residue by silica gel chromatography eluting with 10% methanol in dichloromethane gave the free base of the title compound. The product was dissolved in methanol (1 ml) and treated with a 1M solution hydrochloric acid (36 uL, 0.036 mmol) in diethyl ether and evaporated in vacuo to yield the title compound (14 mg, 32%); MS (ES+) m/e 366 (M+H]+.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was partitioned between ethyl acetate and 2M sodium hydroxide solution
  3. customThe organic phase was separated
  4. washthen washed with water (×3)
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated in vacuo
  7. customPurification of the residue by silica gel chromatography
  8. washeluting with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-f407e609730b430484ac2392d71e9785
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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