Triethylamine → HCID 86632970, compound

HRID 1186273Notes

Reaction equation

HRID 1186273 reaction equation
[CH3:1][NH:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=3)[NH:11][CH:10]=2)[CH2:4]1.CC([O:25][C:26]([O:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=O)(C)C.C(N(CC)CC)C>O1CCOCC1>[C:26](=[O:28])([OH:25])[NH2:2].[CH3:1][N:2]([C@@H:3]1[CH2:8][CH2:7][CH2:6][C@H:5]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=3)[NH:11][CH:10]=2)[CH2:4]1)[C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 57701035HCID 57701035, compound

Product 1

HCID 86632970HCID 86632970, compoundYield 126.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-methyl-3-(5-nitro-1H-indol-3-yl)cyclohexanamine (0.40 g, 1.46 mmol) in 1,4-dioxane (10 mL) was added (Boc)2O (0.35 g, 1.61 mmol) and triethyl amine (0.40 mL, 2.92 mmol) and the resulting mixture left to stir overnight at room temperature. The solvent was evaporated and the crude purified on column chromatography (EtOAc:Hexanes, 1:1) to give the title compound as a yellow solid (0.40 g, 73%). 1H-NMR (CDCl3) δ 1.34-1.44 (m, 1H), 1.49 (s, 9H), 1.57-1.69 (m, 3H), 1.78-1.86 (m, 1H), 1.92-2.00 (m, 1H), 2.03-2.10 (m, 2H), 2.78 (s, 3H), 2.95-3.06 (m, 1H), 3.96-4.27 (m, 1H), 7.11 (d, 1H, J=1.8 Hz), 7.38 (d, 1H, J=9.0 Hz), 8.10 (dd, 1H, J=2.1, 9.0 Hz), 8.37 (s, 1H, NH), 8.61 (d, 1H, J=2.1 Hz); EI-MS (m/z, %), 242 (100), 373 (20).

Workup

  1. waitthe resulting mixture left
  2. customThe solvent was evaporated
  3. customthe crude purified on column chromatography (EtOAc:Hexanes, 1:1)

Sources & evidence

ORD record
ord-5f67079e05e8477fb9f9678b7638320f
Source dataset
uspto-grants-2014_03
Patent number
US08673909B2

Reaction notes

Loading…