Triethylamine → HCID 57899235, compound

HRID 549386Notes

Reaction equation

HRID 549386 reaction equation
[CH3:1][O:2][C:3](=[O:33])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH2:17][CH2:18][C:19]2[C:27]3[C:22](=[CH:23][C:24]([NH2:28])=[CH:25][CH:26]=3)[NH:21][C:20]=2[C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:8][CH:7]=1.[CH3:34][S:35](Cl)(=[O:37])=[O:36].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:33])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH2:17][CH2:18][C:19]2[C:27]3[C:22](=[CH:23][C:24]([NH:28][S:35]([CH3:34])(=[O:37])=[O:36])=[CH:25][CH:26]=3)[NH:21][C:20]=2[C:29]([CH3:30])([CH3:32])[CH3:31])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57899245(E)-3-(4-{1-[2-(6-amino-2-tert-butyl-1H-indol-3-yl)-ethyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl ester

Product 1

HCID 57899235HCID 57899235, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-3-(4-{1-[2-(6-amino-2-tert-butyl-1H-indol-3-yl)-ethyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl ester (0.70 g, 1.6 mmol) in dichloromethane (7 mL) was added methanesulfonyl chloride (0.198 g, 1.73 mmol), triethylamine (241 μL, 1.73 mmol). The resulting solution was stirred at room temperature for 1 h, diluted with ethyl acetate, and washed with 1 N hydrochloric acid, a saturated sodium bicarbonate solution, and a saturated aqueous solution of sodium chloride. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified via silica gel column chromatography to give the title compound (0.21 g, 26% yield). LCMS (m/z): 523.9 (M+1).

Workup

  1. washwashed with 1 N hydrochloric acid
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-9b92df95a2d248518b8724ffc4f78c78
Source dataset
uspto-grants-2011_05
Patent number
US07943652B2

Reaction notes

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