HCID 57701032, compound → HCID 178465427, compound

HRID 1186286Notes

Reaction equation

HRID 1186286 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([N:17]([CH2:25][CH3:26])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:12]1.I.[S:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:33](SC)=[NH:34]>CCO>[CH2:25]([N:17]([CH:13]1[CH2:14][CH2:15][CH2:16][CH:11]([C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:33]([C:29]4[S:28][CH:32]=[CH:31][CH:30]=4)=[NH:34])[CH:3]=3)[NH:7][CH:6]=2)[CH2:12]1)[C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH3:26]

Participants

4

Reactant 2

HCID 57701032HCID 57701032, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178465427HCID 178465427, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl 3-(5-amino-1H-indol-3-yl)cyclohexyl(ethyl)carbamate (0.19 g, 0.53 mmol) in dry EtOH (20 mL) was added methyl thiophene-2-carbimidothioate hydroiodide (0.30 g, 1.06 mmol) and the reaction left to stir at room temperature for 48 hours. The solvent then was evaporated and the mixture dissolved in dichloromethane (20 mL) and washed with 2N NaOH (10 mL). The organic layer was extracted and evaporated. The crude was purified on column chromatography (2 M NH3 in MeOH:CH2Cl2, 2:98 to 5:95) to give the title compound as a yellow solid (0.19 g, 78%). 1H-NMR (DMSO-d6) δ 1.04 (t, 3H, J=6.9 Hz), 1.39 (s, 9H), 1.46-1.57 (m, 3H), 1.57-1.74 (m, 2H), 1.80-1.94 (m, 3H), 2.77-2.89 (m, 1H), 3.13 (q, 2H, J=6.0 Hz), 3.89-4.03 (m, 1H), 6.83 (d, 1H, J=8.4 Hz), 7.13 (s, 1H), 7.22 (dd, 1H, J=4.5, 8.7 Hz), 7.29 (s, 1H), 7.37 (d, 1H, J=8.7 Hz), 7.84 (d, 1H, J=3.3 Hz), 7.88 (d, 1H, J=2.1 Hz), 10.83 (s, 1H, NH); ESI-MS (m/z, %) 467 (MH+, 100).

Workup

  1. waitthe reaction left
  2. customThe solvent then was evaporated
  3. dissolutionthe mixture dissolved in dichloromethane (20 mL)
  4. washwashed with 2N NaOH (10 mL)
  5. extractionThe organic layer was extracted
  6. customevaporated
  7. customThe crude was purified on column chromatography (2 M NH3 in MeOH:CH2Cl2, 2:98 to 5:95)

Sources & evidence

ORD record
ord-b9cba7734f4a4bf7a66ccd7396d964a0
Source dataset
uspto-grants-2014_03
Patent number
US08673909B2

Reaction notes

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