Methyl iodide → HCID 39244464, compound

HRID 2105307Notes

Reaction equation

HRID 2105307 reaction equation
CI.[N+:3]([C:6]1[CH:19]=[CH:18][C:9]([CH2:10][NH:11][CH2:12][C@H:13]2[CH2:17][CH2:16][CH2:15][O:14]2)=[CH:8][CH:7]=1)([O-])=O.[C:20](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:20][N:11]([CH2:10][C:9]1[CH:18]=[CH:19][C:6]([NH2:3])=[CH:7][CH:8]=1)[CH2:12][C@H:13]1[CH2:17][CH2:16][CH2:15][O:14]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 26580537HCID 26580537, compound

Product 1

HCID 39244464HCID 39244464, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (0.728 mL, 11.7 mmol) was added to (4-nitro-benzyl)-[(2R)-tetrahydro-furan-2-ylmethyl]-amine Compound 40b (1.84 g, 7.80 mmol) and potassium carbonate (3.23 g, 23.4 mmol) in DMF (30 mL). After 4 hrs, the reaction is was diluted with water and extracted with ethyl ether. The combined extracts are were washed with water, dried over MgSO4, and evaporated to prepare 1.43 g of methyl-(4-nitro-benzyl)-[(2R)-tetrahydro-furan-2-ylmethyl]-amine Compound 150a. Using the procedure of Example 40, Compound 150a was used in place of (4-nitro-benzyl)-[(2R)-tetrahydro-furan-2-ylmethyl]-amine Compound 40b and carried forward to provide 4-({methyl-[(2R)-tetrahydro-furan-2-ylmethyl]-amino}-methyl)-phenylamine Compound 150b. Using the procedure of Example 1, 5-(5-chloro-2-methoxy-phenyl)-4-oxo-4,5-dihydro-3H-1-thia-3,5, 6,8-tetraaza-acenaphthylene-2-carboxylic acid Compound 147c was used in place of Compound 1 and Compound 150b was used in place of 4-piperidin-1-ylmethyl-phenylamine Compound 1k to give Compound 75. MS 579, 581 (MH+).

Workup

  1. extractionextracted with ethyl ether
  2. washThe combined extracts are were washed with water
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customto prepare 1.43 g of methyl-(4-nitro-benzyl)-[(2R)-tetrahydro-furan-2-ylmethyl]-amine Compound 150a

Sources & evidence

ORD record
ord-12d8494f8d2b401c84f337eb32a04ad0
Source dataset
uspto-grants-2009_08
Patent number
US07579356B2

Reaction notes

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