Pyridine → HCID 69817752, compound

HRID 2417432Notes

Reaction equation

HRID 2417432 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][C:12]1[CH:40]=[CH:39][C:15]([CH2:16][C@H:17]([N:20]([CH2:28][C@H:29]([OH:38])[CH2:30][O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)C(=O)OC(C)(C)C)[CH2:18][OH:19])=[CH:14][CH:13]=1)=[O:10].N1C=CC=CC=1.[CH3:47][S:48](Cl)(=[O:50])=[O:49].[F:52][C:53]([F:58])([F:57])[C:54]([OH:56])=[O:55]>ClCCCl>[F:52][C:53]([F:58])([F:57])[C:54]([OH:56])=[O:55].[OH:19][CH2:18][C@@H:17]([NH:20][CH2:28][C@H:29]([OH:38])[CH2:30][O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:16][C:15]1[CH:39]=[CH:40][C:12]([NH:11][C:9]([NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][S:48]([CH3:47])(=[O:50])=[O:49])=[O:10])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 31297Methanesulfonyl chlorideHCID 69817916HCID 69817916, compound

Product 1

HCID 69817752HCID 69817752, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent4×

Procedure

To a solution of tert-butyl N-[(1S)-1-[4-[[[(2-aminophenyl)amino]carbonyl]amino]benzyl]-2-hydroxyethyl]-N-[(2S)-2-hydroxy-3-phenoxypropyl]carbamate (20.0 mg) in 1,2-dichloroethane (200 μl) were added successively 1.0 M solution of pyridine in 1,2-dichloroethane (54.5 μl) and 1.0 M solution of methanesulfonyl chloride in 1,2-dichloroethane (43.6 μl) at room temperature. After stirring for 2 hours, the solvent was removed by evaporation and the residue was purified by a recycling preparative high pressure liquid chromatography equipped with a gel permeation chromatography column (eluent: chloroform) to give a light brown solid. The solid was dissolved in 1,2-dichloroethane (200 μl). To the solution was added trifluoroacetic acid (200 μl) and the mixture was stirred for 30 minutes. The solvent was removed by evaporation to give N-[2-[[[[4-[(2S)-3-hydroxy-2-[[(2S)-2-hydroxy-3-phenoxypropyl]amino]propyl]phenyl]amino]-carbonyl]amino]phenyl]methanesulfonamide trifluoroacetate (20.3 mg) as a light brown solid.

Workup

  1. customthe solvent was removed by evaporation
  2. customthe residue was purified by a recycling preparative high pressure liquid chromatography
  3. customequipped with a gel permeation chromatography column (eluent: chloroform)
  4. customto give a light brown solid
  5. stirringthe mixture was stirred for 30 minutes
  6. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-cc4739433c884bf6b2495586a443708a
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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