Naratriptan → HCID 14392651, compound

HRID 358595Notes

Reaction equation

HRID 358595 reaction equation
[H-].[Na+].[CH3:3][NH:4][S:5]([CH2:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[CH:19]1[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]1)(=[O:7])=[O:6].[CH3:26]I>CN(C)C=O>[CH3:3][N:4]([CH3:26])[S:5]([CH2:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[CH:19]1[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]1)(=[O:6])=[O:7]

Participants

5

Reactant 3

HCID 4440NaratriptanHCID 6328Methyl iodideHCID 24758Sodium hydride

Product 1

HCID 14392651HCID 14392651, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (60% w/w with paraffin; 124 mg) was added cautiously to a stirred solution the product of Example 1 in dry dimethylformamide (20 ml). The resultant mixture was stirred at room temperature under nitrogen for 0.25 h then a solution of methyl iodide (440 mg) in dry dimethylformamide (1 ml) was added in a stream. The mixture was stirred at room temperature for 2.5 h. The reaction mixture was quenched with water (3 ml), evaporated in vacuo and the residue was chromatographed on silica (150 g), eluting with dichloromethane, ethanol and ammonia (80:10:1) to give a gum. The gum was briefly triturated in diethyl ether and the title compound crystallised out as a powder (238 mg), m.p. 170°-172°.

Workup

  1. customThe reaction mixture was quenched with water (3 ml)
  2. customevaporated in vacuo
  3. customthe residue was chromatographed on silica (150 g)
  4. washeluting with dichloromethane, ethanol and ammonia (80:10:1)
  5. customto give a gum
  6. customThe gum was briefly triturated in diethyl ether
  7. customthe title compound crystallised out as a powder (238 mg), m.p. 170°-172°

Sources & evidence

ORD record
ord-be4515b24ab5459eb3671e6b79142944
Source dataset
uspto-grants-1991_03
Patent number
US04997841

Reaction notes

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