1-(8-Methyl-8-azabicyclo[3.2.1]octan-3-yl)-1H-indol-5-amine → HCID 178479854, compound

HRID 1668478Notes

Reaction equation

HRID 1668478 reaction equation
[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][CH:5]([N:10]1[C:18]3[C:13](=[CH:14][C:15]([NH2:19])=[CH:16][CH:17]=3)[CH:12]=[CH:11]1)[CH2:6]2.I.CS[C:23]([C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)=[NH:24]>C(O)C>[CH3:1][N:2]1[CH:3]2[CH2:9][CH2:8][CH:7]1[CH2:6][CH:5]([N:10]1[C:18]3[C:13](=[CH:14][C:15]([NH:19][C:23]([C:25]4[S:26][CH:27]=[CH:28][CH:29]=4)=[NH:24])=[CH:16][CH:17]=3)[CH:12]=[CH:11]1)[CH2:4]2

Participants

4

Reactant 2

HCID 590046691-(8-Methyl-8-azabicyclo[3.2.1]octan-3-yl)-1H-indol-5-amineHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178479854HCID 178479854, compoundYield 103.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 85 (52 mg, 0.2036 mmol) is charged to a small, argon purged flask fitted with a magnetic stir bar. Anhydrous ethanol (5 mL) and thiophene-2-carboximidothioic acid methyl ester hydroiodide (87.1 mg, 0.3056 mmol) are added to the flask and the reaction was stirred under argon at ambient temperature for 23 hours, at which time the solvent was evaporated and the residue was purified via chromatography on silica gel (methanol:CH2Cl2, 1:9 to 2M NH3 in methanol:CH2Cl2, 5:95) to yield a pale yellow residue, 86 (77 mg, 100%). 1H NMR (major isomer-MeOD) δ 1.81-1.89 (m, 2H), 2.07-2.14 (m, 2H), 2.23-2.31 (m, 2H), 2.48 (s, 3H), 2.69-2.79 (m, 2H), 3.49-3.59 (m, 2H), 4.51-4.61 (m, 1H), 6.58 (d, 1H, J=3.3 Hz), 7.13 (dd, 1H, J=8.7, 1.9 Hz), 7.31-7.34 (m, 1H), 7.54-7.57 (m, 2H), 7.61 (d, 1H, J=3.5 Hz), 7.94-7.97 (m, 2H); ESI-MS (m/z, %): 365 (MH+, 15%), 183 (M++doubly charged, 100%); ESI-HRMS calculated for C21H25N4S (MH+): 365.1794, observed: 365.1784.

Workup

  1. customfitted with a magnetic stir bar
  2. customwas evaporated
  3. customthe residue was purified via chromatography on silica gel (methanol:CH2Cl2, 1:9 to 2M NH3 in methanol:CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-eefdbb6944604558bae7e5358465d64a
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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