Diisopropylethylamine → 5-Chloro-thiophene-2-carboxylic acid [(S)-2-(2-ethyl-3-pyridin-2-yl-benzene-sulfonylamino)-3-((S)-3-methyl-morpholin-4-yl)-3-oxo-propyl]-amide hydro chloride

HRID 389665Notes

Reaction equation

HRID 389665 reaction equation
[CH2:1]([C:3]1[C:8](N2CCOCC2=O)=[CH:7][CH:6]=[CH:5][C:4]=1[S:16]([NH:19][C@H:20]([C:31]([N:33]1[CH2:38][CH2:37][O:36][C@H:35](C)[CH2:34]1)=[O:32])[CH2:21][NH:22][C:23]([C:25]1[S:26][C:27]([Cl:30])=[CH:28][CH:29]=1)=[O:24])(=[O:18])=[O:17])[CH3:2].[CH3:40]CN(C(C)C)C(C)C.C(C1C([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][N:58]=2)=CC=CC=1S(Cl)(=O)=O)C>C(Cl)Cl>[ClH:30].[CH2:1]([C:3]1[C:8]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][N:58]=2)=[CH:7][CH:6]=[CH:5][C:4]=1[S:16]([NH:19][C@H:20]([C:31]([N:33]1[CH2:38][CH2:37][O:36][CH2:35][C@@H:34]1[CH3:40])=[O:32])[CH2:21][NH:22][C:23]([C:25]1[S:26][C:27]([Cl:30])=[CH:28][CH:29]=1)=[O:24])(=[O:17])=[O:18])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 442008575-Chloro-thiophene-2-carboxylic acid [(S)-2-[2-ethyl-3-(3-oxo-morpholin-4-yl)-benzenesulfonylamino]-3-((R)-2-methyl-morpholin-4-yl)-3-oxo-propyl]-amide2×HCID 866532952-Ethyl-3-pyridin-2-yl-benzenesulfonyl chloride

Product 1

HCID 671554425-Chloro-thiophene-2-carboxylic acid [(S)-2-(2-ethyl-3-pyridin-2-yl-benzene-sulfonylamino)-3-((S)-3-methyl-morpholin-4-yl)-3-oxo-propyl]-amide hydro chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Chloro-thiophene-2-carboxylic acid [(S)-2-amino-3-((S)-3-methyl-morpholin-4-yl)-3-oxo-propyl]-amide (Intermediate 3) (95 mg, 0.287 mmol) was dissolved in 2 ml DCM and DIPEA (151 μl, 0.861 mmol). Intermediate 61 (81 mg, 0.287 mmol) in 2 ml DCM was slowly added and the reaction was stirred for 1.5 h. Then the solution was evaporated to dryness and purified by prep. HPLC. After lyophilization the title compound is obtained as colorless, amorphous solid. The material was dissolved in 20 ml water and 150 μl 4N HCl in dioxane were added. The solution was lyophilized again. Yield: 77 mg, 44%. MS (ES+): m/e=577.1/579.1, chloro pattern.

Workup

  1. customThen the solution was evaporated to dryness
  2. custompurified by prep

Sources & evidence

ORD record
ord-0f4a870dd4704cdcb9e18c411f5976a5
Source dataset
uspto-grants-2013_02
Patent number
US08378092B2

Reaction notes

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