Methyl iodide → HCID 58387974, compound

HRID 2079960Notes

Reaction equation

HRID 2079960 reaction equation
[C:1]([O:5][C:6](=[O:32])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:30])[NH:15][CH2:16][C:17]2[S:18][C:19]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)=[CH:20][CH:21]=2)=[C:10]([NH2:31])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].N[C:34]1N=C(N)C=CC=1C(O)=O.CI.[H-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:32])[N:7]([C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:30])[NH:15][CH2:16][C:17]2[S:18][C:19]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)=[CH:20][CH:21]=2)=[C:10]([NH2:31])[N:9]=1)[CH3:34])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 189772452,6-Diaminonicotinic acidHCID 58387970HCID 58387970, compound

Product 1

HCID 58387974HCID 58387974, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (6-amino-5-((5-(3-fluoro-phenoxy)-thiophen-2-ylmethyl)-carbamoyl)-pyridine-2-yl)-carbamic acid tert-butyl ester described in Preparation Example A+-2 (125 mg, 0.27 mmol) and methyl iodide (43 mg, 0.29 mmol) in N,N-dimethylformamide (5 mL) was added sodium hydride (12 mg, 0.29 mmol, 60% in oil) on an ice bath, and the solution was stirred for 1 hour at room temperature. NH silica gel was added to the reaction solution, the solvent was evaporated in vacuo for adsorption, purification was carried out by NH silica gel column chromatography (hexane:ethyl acetate=4:1 then 2:1), and the title compound (87 mg, 0.19 mmol, 70.5%) was obtained as a colorless oil.

Workup

  1. additionNH silica gel was added to the reaction solution
  2. customthe solvent was evaporated in vacuo for adsorption, purification

Sources & evidence

ORD record
ord-09d9c06cd7f143cc851e8b11ef9fe70e
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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