tert-butyl 4-(5-amino-1H-indol-3-yl)piperidine-1-carboxylate → HCID 178451778, compound

HRID 2043510Notes

Reaction equation

HRID 2043510 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][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1.I.CS[C:27]([C:29]1[S:30][CH:31]=[CH:32][CH:33]=1)=[NH:28]>C(O)C>[S:30]1[CH:31]=[CH:32][CH:33]=[C:29]1[C:27](=[NH:28])[NH: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][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 53986362tert-butyl 4-(5-amino-1H-indol-3-yl)piperidine-1-carboxylateHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178451778HCID 178451778, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of compound 86 (0.45 g, 1.426 mmol) in dry ethanol (25 mL) was treated with thiophene-2-carboximidothioic acid methyl ester hydroiodide (0.81 g, 2.853 mmol) at room temperature and resulting solution was stirred for 24 h. The solvent was evaporated, crude was diluted with sat. NaHCO3 solution (25 mL) and CH2Cl2 (50 mL). The organic layer was separated and aqueous layer was extracted into CH2Cl2 (2×25 mL). The combined organic layer was washed with brine (20 mL) and dried (Na2SO4). The solvent was evaporated and the crude product was purified by column chromatography on silica gel (2 M NH3 in methanol: CH2Cl2, 3:97) to obtain compound 87 (0.6 g, quantitative) as a foam. 1H NMR (DMSO-d6) δ 1.40-1.56 (m, 11H), 1.90-1.94 (m, 2H), 2.86-2.94 (m, 3H), 4.02-4.06 (m, 2H), 6.26 (s, 1H), 6.64 (dd, 1H, J=1.2, 8.4 Hz), 6.99 (s, 1H), 7.05 (d, 1H, J=1.8 Hz), 7.09 (dd, 1H, J=3.6, 4.9 Hz), 7.27 (d, 1H, J=8.4 Hz), 7.59 (d, 1H, J=5.1 Hz), 7.71 (d, 1H, J=3.3 Hz), 10.63 (s, 1H); ESI-MS m/z (%): 425 (MH+, 100).

Workup

  1. customresulting solution
  2. customThe solvent was evaporated
  3. additioncrude was diluted with sat. NaHCO3 solution (25 mL) and CH2Cl2 (50 mL)
  4. customThe organic layer was separated
  5. extractionaqueous layer was extracted into CH2Cl2 (2×25 mL)
  6. washThe combined organic layer was washed with brine (20 mL)
  7. dry with materialdried (Na2SO4)
  8. customThe solvent was evaporated
  9. customthe crude product was purified by column chromatography on silica gel (2 M NH3 in methanol: CH2Cl2, 3:97)

Sources & evidence

ORD record
ord-f2c213d8cb8b4e2f9581317ddb2034a3
Source dataset
uspto-grants-2013_11
Patent number
US08586620B2

Reaction notes

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