Ethanolamine → HCID 24750599, compound

HRID 643704Notes

Reaction equation

HRID 643704 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].C(N(CC)CC)C.Cl.[CH:13]1([CH2:16][N:17]2[C:21]3[CH:22]=[CH:23][C:24]([S:26]([C:29]([CH3:34])([CH3:33])[C:30](Cl)=[O:31])(=[O:28])=[O:27])=[CH:25][C:20]=3[N:19]=[C:18]2[CH2:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:15][CH2:14]1>ClCCl>[CH:13]1([CH2:16][N:17]2[C:21]3[CH:22]=[CH:23][C:24]([S:26]([C:29]([CH3:33])([CH3:34])[C:30]([NH:4][CH2:3][CH2:1][OH:2])=[O:31])(=[O:28])=[O:27])=[CH:25][C:20]=3[N:19]=[C:18]2[CH2:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 86630621HCID 86630621, compound

Product 1

HCID 24750599HCID 24750599, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of ethanolamine (54 mg, 0.886 mmol), triethylamine (0.184 mL, 1.32 mmol) and dichloromethane (3 mL) was added a solution of 2-{[1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazol-5-yl]sulfonyl}-2-methylpropanoyl chloride hydrochloride (Step A of Example 7, 198 mg, 0.443 mmol) in dichloromethane (2 mL) at room temperature. After stirring at the same temperature for 1 h, the mixture was concentrated under reduced pressure. The residue was purified by HPLC (ODS, gradient elution with acetonitrile/0.01% aq. NH3=4:96 to 96:4, by volume; flow rate 40 mL/min) to afford the title compound (105 mg, 55%) as an amorphous.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customThe residue was purified by HPLC (ODS, gradient elution with acetonitrile/0.01% aq. NH3=4:96 to 96:4, by volume; flow rate 40 mL/min)

Sources & evidence

ORD record
ord-a66eb5e055e949c597f7695f10df363e
Source dataset
uspto-grants-2010_04
Patent number
US07700618B2

Reaction notes

Loading…