tert-Butyl 4-(5-amino-1H-indol-3-yl)cyclohex-3-enyl(methyl)carbamate → HCID 178486004, compound

HRID 2043515Notes

Reaction equation

HRID 2043515 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][C: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)=[CH: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 178486004HCID 178486004, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of compound 98 (0.415 g, 1.215 mmol) in dry ethanol (20 mL) was treated with thiophene-2-carboximidothioic acid methyl ester hydroiodide (0.693 g, 2.430 mmol) at room temperature and the resulting solution was stirred for 24 h. The solvent was evaporated and crude was diluted with sat. NaHCO3 solution (25 mL) and CH2Cl2 (50 mL). The organic layer was separated and aqueous layer was extracted with CH2Cl2 (2×25 mL). The combined organic layer was washed with brine (20 mL) and dried (Na2SO4). The solvent was evaporated and crude product was purified by column chromatography on silica gel (2M NH3 in methanol: CH2Cl2, 5:95) to obtain compound 99 (0.37 g, 68%) as a foam. 1H NMR (DMSO-d6) δ: 0.85 (t, 1H, J=7.2 Hz), 1.20-1.26 (m, 1H), 1.40 (s, 9H), 1.77-1.87 (m, 2H), 2.22-2.40 (m, 2H), 2.72 (s, 3H), 4.06-4.16 (m, 1H), 6.06 (s, 1H), 6.28 (brs, 1H), 6.66 (d, 1H, J=8.4 Hz), 7.10 (t, 1H, J=4.2 Hz), 7.22 (s, 1H), 7.25-7.32 (m, 2H), 7.60 (d, 1H, J=4.8 Hz), 7.72 (d, 1H, J=3.3 Hz), 10.94 (s, 1H); ESI-MS m/z (%): 451 (MH+, 100).

Workup

  1. customThe solvent was evaporated
  2. additioncrude was diluted with sat. NaHCO3 solution (25 mL) and CH2Cl2 (50 mL)
  3. customThe organic layer was separated
  4. extractionaqueous layer was extracted with CH2Cl2 (2×25 mL)
  5. washThe combined organic layer was washed with brine (20 mL)
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was evaporated
  8. customcrude product was purified by column chromatography on silica gel (2M NH3 in methanol: CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-5fc06c2b928c41fbb34c463e7be4484b
Source dataset
uspto-grants-2013_11
Patent number
US08586620B2

Reaction notes

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