HCID 66704640, compound → HCID 178464393, compound

HRID 424558Notes

Reaction equation

HRID 424558 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]2[S:6][CH2:7][CH2:8][N:9]([CH2:10][CH2:11][N:12]([CH2:20][CH3:21])[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:4]=2[CH:3]=1.I.[S:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[C:30](SC)=[NH:31]>C(O)C.C(OCC)(=O)C>[CH2:20]([N:12]([CH2:11][CH2:10][N:9]1[CH2:8][CH2:7][S:6][C:5]2[CH:22]=[CH:23][C:2]([NH:1][C:30]([C:26]3[S:25][CH:29]=[CH:28][CH:27]=3)=[NH:31])=[CH:3][C:4]1=2)[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:21]

Participants

5

Reactant 2

HCID 66704640HCID 66704640, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178464393HCID 178464393, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of tert-butyl 2-(6-amino-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl(ethyl)carbamate (800 mg, 2.371 mmol) in ethanol (8 mL) was added methyl thiophene-2-carbimidothioate hydroiodide (1.014 g, 3.56 mmol). The resulting mixture was stirred at room temperature for 3 hours. The mixture was then diluted with ethyl acetate and washed with saturated sodium carbonate (3×). The organic phase was dried, filtered, concentrated, and then chromatographed in 1:1 hexanes:ethyl acetate giving the desired product (415 mg, 39.2%). 1H NMR (DMSO-d6) δ 7.70 (d, J=3.0 Hz, 1H), 7.58 (d, J=2.4 Hz, 1H), 7.49-7.44 (m, 1H), 7.07 (t, J=4.4 Hz, 1H), 6.84 (d, J=7.8 Hz, 1H), 6.35-6.26 (m, 2H), 6.08 (d, J=7.5 Hz, 1H), 3.64-3.49 (m, 2H), 3.45-3.25 (m, 4H), 3.24-3.12 (m, 2H), 3.01-2.85 (m, 2H), 1.39-1.29 (m, 9H), 1.02 (t, J=6.9 Hz, 3H); ESI-MS (m/z, %): 447 (MH+, 100).

Workup

  1. washwashed with saturated sodium carbonate (3×)
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed in 1:1 hexanes

Sources & evidence

ORD record
ord-0f7e0acdda804d80af059891e74750a5
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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