1-Iodoheptane → HCID 54291006, compound

HRID 1712122Notes

Reaction equation

HRID 1712122 reaction equation
[CH3:1][N:2]([CH3:15])[C:3](=[O:14])[NH:4][C:5]1[S:9][N:8]=[C:7]([OH:10])[C:6]=1[C:11]([NH2:13])=[O:12].CC([O-])(C)C.[K+].I[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>CN(C=O)C.CCCCCC.C(OCC)(=O)C.CO.C(O)(=O)C>[CH3:1][N:2]([CH3:15])[C:3](=[O:14])[NH:4][C:5]1[S:9][N:8]=[C:7]([O:10][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:6]=1[C:11]([NH2:13])=[O:12]

Participants

6

Reactant 3

HCID 202741-IodoheptaneHCID 23665647Potassium tert-butoxideHCID 178484693HCID 178484693, compound

Product 1

HCID 54291006HCID 54291006, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 18469568HCID 18469568, compoundSolvent

Procedure

A suspension of 5-(3,3-Dimethyl-ureido)-3-hydroxy-isothiazole-4-carboxylic acid amide (200 mg, 0.87 mmol) in DMF (5 mL) was treated with KOtBu (107 mg, 0.96 mmol) at ambient temperature causing complete dissolution. Next was added 1-iodoheptane (1 mL) and the reaction stirred at ambient temperature until complete disappearance of starting materials as measured by TLC using hexane/ethyl acetate/methanol/acetic acid (48/48/2/2) as eluent. The reaction mixture was then concentrated by rotary evaporation under high vacuum, the residue dissolved in ethyl acetate and methanol, and was then purified via radial chromatography (2 mm plate) using the same eluent as for TLC affording two components. The more polar material was identified as the N-alkylated adduct (102 mg, 0.311 mmol, 36%). 1H NMR (400 MHz, CDCl3) δ 0.86 (t, J=6.7 Hz, 3H), 1.25-1.31 (m, 8H), 1.64-1.70 (m, 2H), 3.07 (s, 6H), 3.68 (t, J=7.2 Hz, 2H), 5.40 (s, 1H), 8.86 (s, 1H), 12.1 (s, 1H) ppm; 13C NMR (101 MHz, CDCl3) δ 13.94, 22.45, 26.48, 28.74, 29.52, 31.52, 36.11, 42.54, 166.99 ppm; MS (APCI, m/z): 329 [M+H]+. The less polar material was the O-alkylated adduct (134 mg, 0.408 mmol, 48%). 1H NMR (400 MHz, CDCl3) δ 0.88 (t, J=6.8 Hz, 3H), 1.24-1.50 (m, 8H), 1.75-1.88 (m, 2H), 3.07 (s, 6H), 4.43 (t, J=6.7 Hz, 2H), 5.42 (s, 1H), 7.25 (s, 1H appears to be superimposed on CDCl3 peak), 11.6 (s, 1H) ppm; 13C NMR (101 MHz, CDCl3) δ 13.94, 22.45, 25.86, 28.83, 31.60, 36.11, 68.69, 97.69, 154.15, 162.27, 166.20, 169.45 ppm; MS (APCI, m/z): 329 [M+H]+.

Workup

  1. dissolutiondissolution
  2. concentrationThe reaction mixture was then concentrated by rotary evaporation under high vacuum
  3. dissolutionthe residue dissolved in ethyl acetate
  4. custommethanol, and was then purified via radial chromatography (2 mm plate)
  5. customaffording two components

Sources & evidence

ORD record
ord-aa45265987c54c29aa7c1ef2cdc91330
Source dataset
uspto-grants-2010_09
Patent number
US07790902B2

Reaction notes

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