Methyl iodide → HCID 22277865, compound

HRID 1063885Notes

Reaction equation

HRID 1063885 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([I:18])[C:12]=1[O:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:5][N:6]([OH:9])[CH:7]=[O:8].[C:19](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[CH2:14]([O:13][C:12]1[C:2]([NH:1][CH3:19])=[CH:3][C:4]([CH2:5][N:6]([OH:9])[CH:7]=[O:8])=[CH:10][C:11]=1[I:18])[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22277860HCID 22277860, compound

Product 1

HCID 22277865HCID 22277865, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(3-amino-4-butoxy-5-iodo-benzyl)-N-hydroxy-formamide (36 mg, 0.1 mmol), potassium carbonate (11 mg, 0.11 mmol) and iodomethane (9.2 ul, 0.15 mmol) in DMF (1 ml) was stirred 18 h at room temperature. The mixture was partitioned between ethyl acetate and water, the organic extract was washed with brine then dried with sodium sulfate and all voltiles removed. Purification by preparative HPLC afforded the title compound (8 mg, 22%) 1H NMR (400 MHz, CD3OD) δ 8.36* 7.16 (s, 1H), 7.00 (s, 1H), 6.59 (s, 1H), 4.58* 4.54 (s, 2H) 3.84 (t, j=6.2 Hz, 2H), 2.83* 2.81 (s, 3H) 1.83-1.87 (m, 2H), 1.54-1.59 (m, 2H), 1.03 (t, j=7.1 Hz, 3H). M+1=379.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. extractionthe organic extract
  3. washwas washed with brine
  4. dry with materialthen dried with sodium sulfate
  5. customall voltiles removed
  6. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-2e1bf5f392be4ea69e41c09ba96150e2
Source dataset
uspto-grants-2005_11
Patent number
US06967220B2

Reaction notes

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