Methyl iodide → tert-butyl N-[4-[3-(2-chlorophenyl)-5-methoxyphenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

HRID 723045Notes

Reaction equation

HRID 723045 reaction equation
IC.[F-].[CH2:4]([N+](CCCC)(CCCC)CCCC)CCC.[C:21]([O:25][C:26](=[O:54])[NH:27][C:28]([C:30]1[S:31][C:32]([S:52][CH3:53])=[C:33]([S:35]([C:38]2[CH:39]=[C:40]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=3[Cl:51])[CH:41]=[C:42]([OH:44])[CH:43]=2)(=[O:37])=[O:36])[CH:34]=1)=[NH:29])([CH3:24])([CH3:23])[CH3:22]>C1COCC1.CCOC(C)=O>[C:21]([O:25][C:26](=[O:54])[NH:27][C:28]([C:30]1[S:31][C:32]([S:52][CH3:53])=[C:33]([S:35]([C:38]2[CH:39]=[C:40]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=3[Cl:51])[CH:41]=[C:42]([O:44][CH3:4])[CH:43]=2)(=[O:36])=[O:37])[CH:34]=1)=[NH:29])([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 2724141Tetrabutylammonium FluorideHCID 145857663tert-butyl N-[4-[3-(2-chlorophenyl)-5-hydroxyphenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 145857682tert-butyl N-[4-[3-(2-chlorophenyl)-5-methoxyphenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamateYield 62.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Iodomethane (3 μL, 0.045 mmol) and tetrabutylammonium fluoride (1M in THF, 14 μL, 0.014 mmol) was added to a solution of {[4-(2′-chloro-5-hydroxy-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester ((Example 19: step b) 5 mg, 0.009 mmol) in THF. After stirring for 2 hours, the solution was diluted with EtOAc (20 mL). The organic layer was washed with water (2×4 mL) and brine (5 mL), and was dried over MgSO4. Removal of the solvent in vacuo followed by purification of the residue (preparative TLC; 30% EtOAc in hexanes) afforded the title compound (3.1 mg, 62%). 1H-NMR (CDCl3): δ 7.84 (s, 1H), 7.64 (t, 1H, J=1.6 Hz), 7.53 (dd, 1H, J=1.6, 2.6 Hz), 7.47 (m, 1H), 7.33 (m, 3H), 7.21 (dd, 1H, J=1.6, 2.6 Hz), 3.89 (s, 3H), 2.60 (s, 3H), 1.52 (s, 9H). ESI-MS (m/z): Calcd. for C13H13BrN2O3S3: 421.4; found: 421.1.

Workup

  1. washThe organic layer was washed with water (2×4 mL) and brine (5 mL)
  2. dry with materialwas dried over MgSO4
  3. customRemoval of the solvent in vacuo
  4. customfollowed by purification of the residue (preparative TLC; 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5aee114fe593436eb762948011dc5269
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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