HCID 66704634, compound → HCID 178484225, compound

HRID 424575Notes

Reaction equation

HRID 424575 reaction equation
[CH3:1][N:2]([CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][S:15][C:14]2[CH:18]=[CH:19][C:20]([N+:22]([O-])=O)=[CH:21][C:13]1=2)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].I.[S:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[C:31](SC)=[NH:32]>C(O)C.[Pd]>[CH3:1][N:2]([CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][S:15][C:14]2[CH:18]=[CH:19][C:20]([NH:22][C:31]([C:27]3[S:26][CH:30]=[CH:29][CH:28]=3)=[NH:32])=[CH:21][C:13]1=2)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6]

Participants

5

Reactant 2

HCID 66704634HCID 66704634, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178484225HCID 178484225, compoundYield 52.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A stirred suspension of tert-butyl methyl(2-(6-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl)carbamate (650 mg, 1.839 mmol) and palladium, 10 wt. % on activated carbon (196 mg, 0.184 mmol) in ethanol (10 mL) was stirred under an atmosphere of hydrogen (balloon pressure) at room temperature for 2 hours. To the mixture was then added methyl thiophene-2-carbimidothioate hydroiodide (787 mg, 2.76 mmol), and the resulting suspension was stirred at room temperature overnight. The mixture was filtered to remove palladium, diluted with water and saturated sodium carbonate, and then extracted with dichloromethane (3×). The combined organics were dried, filtered, concentrated, and then chromatographed in 2:3 ethyl acetate:hexanes to afford the desired product (420 mg, 52.8%). 1H NMR (DMSO-d6) δ 7.72-7.68 (m, 1H), 7.58 (d, J=5.1 Hz, 1H), 7.09-7.05 (m, 1H), 6.84 (d, J=7.8 Hz, 1H), 6.38-6.21 (m, 3H), 6.08 (d, J=8.4 Hz, 1H), 3.64-3.56 (m, 2H), 3.42-3.33 (m, 4H), 3.03-2.94 (m, 2H), 2.81 (s, 3H), 1.36-1.22 (m, 9H); ESI-MS (m/z, %): 433 (MH+, 100).

Workup

  1. filtrationThe mixture was filtered
  2. customto remove palladium
  3. additiondiluted with water and saturated sodium carbonate
  4. extractionextracted with dichloromethane (3×)
  5. customThe combined organics were dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed in 2:3 ethyl acetate

Sources & evidence

ORD record
ord-8a0cd05f82f040f3add8884e2b920389
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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