Triethylamine → HCID 46929287, compound

HRID 1506681Notes

Reaction equation

HRID 1506681 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[OH:6][CH2:7][CH2:8][N:9]1[C:21]2[CH2:20][CH2:19][CH2:18][CH:17]([C:22](O)=[O:23])[C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][C:14]=2[O:25][CH3:26].[CH3:27][S:28](Cl)(=[O:30])=[O:29].C(N(CC)CC)C>ClCCl>[CH2:1]([N:3]([CH2:4][CH3:5])[C:22]([CH:17]1[C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[O:25][CH3:26])[N:9]([CH2:8][CH2:7][O:6][S:28]([CH3:27])(=[O:30])=[O:29])[C:21]=2[CH2:20][CH2:19][CH2:18]1)=[O:23])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66679053HCID 66679053, compound

Product 1

HCID 46929287HCID 46929287, compoundYield 117.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9-(2-Hydroxyethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid diethylamine (11) (478 mg, 1.4 mmol) in dichloromethane (30 ml) was cooled to 0° C. and methanesulfonyl chloride (477 mg, 4.2 mmol, 324 μL) and triethylamine (420 mg, 4.2 mmol, 578 μL) were added and allowed to warm to RT overnight. The reaction was washed with 5% aqueous potassium carbonate solution. The layers were separated. The combined organics were dried over magnesium sulfate and concentrated in vacuo to give a gum (696 mg). The crude material was purified by silica gel chromatography eluting with petrol (A): ethyl acetate (B) (75-100% B, 22 CV, 120 g, 85 mL/min) to afford Methanesulphonic acid 2-(4-diethylcarbamyl-5-methoxy-1,2,3,4-tetrahydro-carbazol-9-yl)ethyl ester (precursor compound 5) as a gum that crystallised from diethyl ether to give 346 mg (59%) of a colourless solid. The structure was confirmed by 13C NMR (75 MHz; CDCl3): δC 13.1, 14.5, 20.0, 21.9, 28.0, 36.3, 36.7, 40.3, 41.8, 41.9, 54.7, 68.1, 100.0, 102.0, 109.0, 116.4, 122.0 135.1, 137.3, 153.8, and 174.6.

Workup

  1. washThe reaction was washed with 5% aqueous potassium carbonate solution
  2. customThe layers were separated
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4e6042091b6c44a7880e40da45c67daa
Source dataset
uspto-grants-2015_12
Patent number
US09220795B2

Reaction notes

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