tert-Butyl 4-(5-amino-1H-indol-3-yl)cyclohex-3-enyl(methyl)carbamate → HCID 178486005, compound

HRID 552941Notes

Reaction equation

HRID 552941 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[C:11]1[CH2:16][CH2:15][CH:14]([N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13][CH:12]=1.I.CS[C:29]([C:31]1[S:32][CH:33]=[CH:34][CH:35]=1)=[NH:30]>C(O)C>[CH3:25][N:17]([CH:14]1[CH2:15][CH2:16][CH:11]([C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:29]([C:31]4[S:32][CH:33]=[CH:34][CH:35]=4)=[NH:30])[CH:3]=3)[NH:7][CH:6]=2)[CH2:12][CH2:13]1)[C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 57384541tert-Butyl 4-(5-amino-1H-indol-3-yl)cyclohex-3-enyl(methyl)carbamateHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178486005HCID 178486005, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of compound 82 (0.44 g, 1.281 mmol) in dry ethanol (20 mL) was treated with thiophene-2-carboximidothioic acid methyl ester hydroiodide (0.73 g, 2.562 mmol) at room temperature and stirred for 24 h. The solvent was evaporated and product was precipitated with ether (100 mL). The solid was dissolved into sat. NaHCO3 sol.: CH2Cl2 (50 mL, 1:1). The org. layer was separated and aqueous layer was extracted with CH2Cl2 (2×25 mL). The combined CH2Cl2 layer was washed with brine (20 mL) and dried (Na2SO4). The solvent was evaporated and crude was purified by column chromatography (2M NH3 in methanol: CH2Cl2, 5:95) to obtain compound 83 (0.425 g, 73%) as a foam in 1:2 ration of diastereomers. 1H NMR (DMSO-d6) δ 1.38-1.56 (m, 11H), 1.64-1.82 (m, 4H), 2.06-2.18 (m, 2H), 2.62-2.70 (m, 4H), 3.80-3.90 (m, 1H), 6.27 (brs, 1H), 6.62-6.66 (m, 1H), 6.95-7.11 (m, 3H), 7.22-7.29 (m, 1H), 7.59 (d, 1H, J=5.1 Hz), 7.71 (d, 1H, J=3.6 Hz), 10.59, 10.63 (2s, 1H); ESI-MS m/z (%): 453 (MH+, 100).

Workup

  1. customThe solvent was evaporated
  2. customproduct was precipitated with ether (100 mL)
  3. dissolutionThe solid was dissolved into sat. NaHCO3 sol.
  4. customlayer was separated
  5. extractionaqueous layer was extracted with CH2Cl2 (2×25 mL)
  6. washThe combined CH2Cl2 layer was washed with brine (20 mL)
  7. dry with materialdried (Na2SO4)
  8. customThe solvent was evaporated
  9. customcrude was purified by column chromatography (2M NH3 in methanol: CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-087789c3784447be90a57101a4585d9b
Source dataset
uspto-grants-2011_05
Patent number
US07951940B2

Reaction notes

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