HCID 57701025, compound → HCID 178486007, compound

HRID 1186280Notes

Reaction equation

HRID 1186280 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]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:12]1.I.[S:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[C:32](SC)=[NH:33]>CCO>[CH3:25][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:32]([C:28]4[S:27][CH:31]=[CH:30][CH:29]=4)=[NH:33])[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]

Participants

4

Reactant 2

HCID 57701025HCID 57701025, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178486007HCID 178486007, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl 3-(5-amino-1H-indol-3-yl)cyclohexyl(methyl)carbamate (0.57 g, 1.66 mmol) in dry EtOH (25 mL) was added methyl thiophene-2-carbimidothioate hydroiodide (0.75 g, 3.32 mmol) and the reaction left to stir at room temperature for 48 h. 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 (0.62 g, 81%). 1H-NMR (DMSO-d6) δ 1.35 (s, 9H), 1.42-1.71 (m, 5H), 1.88-1.93 (m, 2H), 1.98-2.04 (m, 1H), 2.69 (s, 3H), 3.40-3.53 (m, 1H), 4.24-4.27 (m, 1H), 6.22 (s, 2H, NH), 6.64 (dd, 1H, J=1.8, 8.4 Hz), 6.93 (s, 1H), 7.09 (dd, 1H, J=3.6, 5.1 Hz), 7.28 (d, 2H, J=8.4 Hz), 7.58 (d, 1H, J=4.5 Hz), 7.70 (d, 1H, J=3.6 Hz), 10.68 (s, 1H, NH); ESI-MS (m/z, %) 453 (MNa+, 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-98c3c82fef1941f2ba9186c2791f94da
Source dataset
uspto-grants-2014_03
Patent number
US08673909B2

Reaction notes

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