5-(2-Pyridyl)thiophene-2-sulfonyl chloride → (R)-benzyl 4-(dimethylamino)-3-(5-(pyridin-2-yl)thiophene-2-sulfonamido)butanoate

HRID 1958719Notes

Reaction equation

HRID 1958719 reaction equation
[NH2:1][C@@H:2]([CH2:14][N:15]([CH3:17])[CH3:16])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]1[S:28][C:27]([S:29](Cl)(=[O:31])=[O:30])=[CH:26][CH:25]=1>>[CH3:17][N:15]([CH3:16])[CH2:14][C@H:2]([NH:1][S:29]([C:27]1[S:28][C:24]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=2)=[CH:25][CH:26]=1)(=[O:30])=[O:31])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]

Participants

3

Reactant 2

HCID 27372315-(2-Pyridyl)thiophene-2-sulfonyl chlorideHCID 46223508(R)-benzyl 3-amino-4-(dimethylamino)butanoate

Product 1

HCID 86641217(R)-benzyl 4-(dimethylamino)-3-(5-(pyridin-2-yl)thiophene-2-sulfonamido)butanoateYield 40%

Procedure

According to the method described in example S20a, (R)-benzyl 3-amino-4-(dimethylamino)butanoate (27 mg, 0.086 mmol) was reacted with 5-(pyridin-2-yl)thiophene-2-sulfonyl chloride to yield the title compound as a white solid (16 mg, 40%). MS ESI 460.2 [M+H]+, calcd for [C22H25N3O4S2+H]+ 460.13

Sources & evidence

ORD record
ord-35fdec3179e54deeb5441cc3401fb14a
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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