HCID 59144181, compound → HCID 178452059, compound

HRID 424582Notes

Reaction equation

HRID 424582 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][C:7]2[S:8][CH2:9][CH2:10][N:11]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[C:6]=2[CH:5]=1)([O-])=O.I.[S:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:33](SC)=[NH:34]>C(O)C.O1CCCC1.C(OCC)(=O)C.[Pd]>[S:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:33](=[NH:34])[NH:1][C:4]1[CH:26]=[CH:25][C:7]2[S:8][CH2:9][CH2:10][N:11]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[C:6]=2[CH:5]=1

Participants

7

Reactant 2

HCID 59144181HCID 59144181, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178452059HCID 178452059, compoundYield 71.3%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of tert-butyl 4-(6-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)piperidine-1-carboxylate (468 mg, 1.233 mmol) and palladium, 10 wt. % on activated carbon (131 mg, 0.123 mmol) in ethanol (10 mL) and tetrahydrofuran (1 mL) was stirred under an atmosphere of hydrogen (balloon pressure) for 2 hours. During this time, the reaction mixture turned colorless. To the mixture was then added methyl thiophene-2-carbimidothioate hydroiodide (528 mg, 1.850 mmol), and the resulting suspension was stirred at room temperature overnight. The mixture was then diluted with ethyl acetate and filtered through a pad of Celite. The filtrate was washed with saturated sodium carbonate (3×). The organic phase was dried, filtered, concentrated, and then chromatographed in 1:5 ethyl acetate:dichloromethane to give the desired product (403 mg, 71.2%). 1H NMR (DMSO-d6) δ 7.72 (d, J=3.0 Hz, 1H), 7.59 (d, J=5.1 Hz, 1H), 7.10-7.06 (m, 1H), 6.86 (d, J=8.1 Hz, 1H), 6.42-6.28 (m, 3H), 6.13 (d, J=8.1 Hz, 1H), 4.06-3.95 (m, 2H), 3.85-3.76 (m, 1H), 3.40-3.33 (m, 2H), 2.99-2.93 (m, 2H), 2.92-2.75 (m, 2H), 1.69-1.48 (m, 4H), 1.39 (s, 9H); ESI-MS (m/z, %): 459 (MH+, 100).

Workup

  1. filtrationfiltered through a pad of Celite
  2. washThe filtrate was washed with saturated sodium carbonate (3×)
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed in 1:5 ethyl acetate

Sources & evidence

ORD record
ord-f1f4ab0c82c643b8a5bc2bda0a711fab
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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