Dichloromethane → HCID 131726702, compound

HRID 968644Notes

Reaction equation

HRID 968644 reaction equation
[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:17][CH3:18])[C:10]([C:19]([OH:21])=O)=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:22][CH:23]1[CH2:28][NH:27][CH2:26][CH:25]([CH3:29])[NH:24]1.C(N=C=NC(C)C)(C)C.ON1C2C=CC=CC=2N=N1.[Cl:49]CCl>>[ClH:49].[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:17][CH3:18])[C:10]([C:19]([N:27]3[CH2:26][CH:25]([CH3:29])[NH:24][CH:23]([CH3:22])[CH2:28]3)=[O:21])=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 12734DiisopropylcarbodiimideHCID 660562,6-DimethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 686950531-(Cyclohexylmethyl)-7-methoxyindole-3-carboxylic acid

Product 1

HCID 131726702HCID 131726702, compound

Procedure

To a solution of 1-(cyclohexylmethyl)-7-methoxy-indole-3-carboxylic acid (0.25 g, 0.87 mmol, prepared following the method in Example 1) and 2,6-dimethylpiperazine (0.12 g, 1.05 mmol) in dichloromethane (10 ml) was added diisopropylcarbodiimide (0.16 ml, 1.05 mmol) and 1-hydroxybenzotriazole (0.01 g, 0.09 mmol). The mixtures was stirred at room temperature for 18 h. The mixture was washed with 5 M sodium hydroxide (2×10 ml), dried with magnesium sulfate and evaporated. The residue was purified by flash chromatography eluting with 5-10% (v/v) methanol in dichloromethane to afford the title compound (free base) as a colourless oil. The free base (0.15 g) was dissolved in diethyl ether (3 ml) and treated dropwise with 2 M hydrochloric acid in diethyl ether (1 ml). The resulting precipitate was collected by filtration, washed with diethyl ether (15 ml) and dried under reduced pressure to afford the title compound (1:1 hydrochloric acid salt) as a colourless solid (0.15 g, 0.36 mmol). 1H NMR (400 MHz, CD3OD) δH 0.98-1.26 (5H, m) 1.32 (6H, d, J 6.5), 1.56 (2H, brd, J 12.0), 1.62-1.90 (4H, m), 3.06 (2H, dd, J 14.5, 11.5), 3.39-3.50 (2H, m), 3.95 (3H, s), 4.26 (2H, d, J 7.5), 4.52 (2H, br d, J 13.5), 6.77 (1H, d, J 7.5), 7.1 (1H, t, J 8.0), 7.24 (1H, d, J 8.0), 7.54 (1H, s); EIMS: m/z 384.2 [M+H]+.

Workup

  1. washThe mixture was washed with 5 M sodium hydroxide (2×10 ml)
  2. dry with materialdried with magnesium sulfate
  3. customevaporated
  4. customThe residue was purified by flash chromatography
  5. washeluting with 5-10% (v/v) methanol in dichloromethane

Sources & evidence

ORD record
ord-2be08c29232d4d4482abb771b6ddd7b5
Source dataset
uspto-grants-2007_12
Patent number
US07304064B2

Reaction notes

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