Diisopropylethylamine → 5-Chloro-thiophene-2-carboxylic acid [(S)-2-[3-(5-chloro-1-methyl-2-oxo-1,2-dihydro-pyridin-3-yl)-2-ethyl-benzenesulfonylamino]-3-((S)-3-methyl-morpholin-4-yl)-3-oxo-propyl]-amide

HRID 389666Notes

Reaction equation

HRID 389666 reaction equation
[NH2:1][C@H:2]([C:13]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][C@@H:16]1[CH3:21])=[O:14])[CH2:3][NH:4][C:5]([C:7]1[S:8][C:9]([Cl:12])=[CH:10][CH:11]=1)=[O:6].C(C1C(N2CCOCC2=O)=CC=CC=1S(N[C@H](C(N1CCO[C@H](C)C1)=O)CNC(C1SC(Cl)=CC=1)=O)(=O)=O)C.CCN(C(C)C)C(C)C.[Cl:70][C:71]1[CH:72]=[C:73]([C:79]2[C:80]([CH2:89][CH3:90])=[C:81]([S:85](Cl)(=[O:87])=[O:86])[CH:82]=[CH:83][CH:84]=2)[C:74](=[O:78])[N:75]([CH3:77])[CH:76]=1>C(Cl)Cl.O1CCOCC1.C(Cl)Cl>[Cl:70][C:71]1[CH:72]=[C:73]([C:79]2[C:80]([CH2:89][CH3:90])=[C:81]([S:85]([NH:1][C@H:2]([C:13]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][C@@H:16]3[CH3:21])=[O:14])[CH2:3][NH:4][C:5]([C:7]3[S:8][C:9]([Cl:12])=[CH:10][CH:11]=3)=[O:6])(=[O:86])=[O:87])[CH:82]=[CH:83][CH:84]=2)[C:74](=[O:78])[N:75]([CH3:77])[CH:76]=1

Participants

7

Reactant 4

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]-amideHCID 671552485-Chloro-thiophene-2-carboxylic acid [(S)-2-amino-3-((S)-3-methyl-morpholin-4-yl)-3-oxo-propyl]-amideHCID 867617693-(5-Chloro-1-methyl-2-oxo-1,2-dihydro-pyridin-3-yl)-2-ethyl-benzenesulfonyl chloride

Product 1

HCID 442009775-Chloro-thiophene-2-carboxylic acid [(S)-2-[3-(5-chloro-1-methyl-2-oxo-1,2-dihydro-pyridin-3-yl)-2-ethyl-benzenesulfonylamino]-3-((S)-3-methyl-morpholin-4-yl)-3-oxo-propyl]-amide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 18626912Dioxane methylene chlorideSolvent

Procedure

5-Chloro-thiophene-2-carboxylic acid [(S)-2-amino-3-((S)-3-methyl-morpholin-4-yl)-3-oxo-propyl]-amide, Intermediate 3 (78 mg, 0.235 mmol) was dissolved in 3 ml DCM/1,4-Dioxane (1:1) and DIPEA (164 μl, 0.94 mmol). Intermediate 65 (82 mg, 0.235 mmol) in 1.5 ml DCM was slowly added and the reaction was stirred for 2 h. Then the solution was evaporated to dryness and purified by prep. HPLC. After lyophilization the title compound is obtained as colorless, amorphous solid.

Workup

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

Sources & evidence

ORD record
ord-9fddb28066184426add19ff0ba2ef4d1
Source dataset
uspto-grants-2013_02
Patent number
US08378092B2

Reaction notes

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