5'-Chloro-2,2'-bithiophene-5-sulfonyl chloride → 5'-Chloro-[2,2']bithiophenyl-5-sulfonic acid [2-oxo-1-(1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-pyrrolidin-3(S)-yl]-amide

HRID 394613

Reaction equation

HRID 394613 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[S:8][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:10][CH:11]=2)=[CH:4][CH:3]=1.C(OC([N:23]1[C:31]2[CH:30]=[CH:29][N:28]=[CH:27][C:26]=2[CH:25]=[C:24]1[CH2:32][N:33]1[CH2:37][CH2:36][C@H:35]([NH2:38])[C:34]1=[O:39])=O)(C)(C)C>>[O:39]=[C:34]1[C@@H:35]([NH:38][S:12]([C:9]2[S:8][C:7]([C:5]3[S:6][C:2]([Cl:1])=[CH:3][CH:4]=3)=[CH:11][CH:10]=2)(=[O:14])=[O:13])[CH2:36][CH2:37][N:33]1[CH2:32][C:24]1[NH:23][C:31]2[CH:30]=[CH:29][N:28]=[CH:27][C:26]=2[CH:25]=1

Participants

3

Reactant 2

HCID 220172805'-Chloro-2,2'-bithiophene-5-sulfonyl chlorideHCID 54368269HCID 54368269, compound

Product 1

HCID 100744105'-Chloro-[2,2']bithiophenyl-5-sulfonic acid [2-oxo-1-(1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-pyrrolidin-3(S)-yl]-amide

Procedure

The title compound is prepared as described in EXAMPLE 56, Part A using 5′-chloro-[2,2′]bithiophenyl-5-sulfonyl chloride and 2-[3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester as starting material. The crude product can be purified by column chromatography eluting with 5% MeOH/CH2Cl2to give the title compound as a white solid or used in the subsequent step after an aqueous work-up without further purification. Ion spray MS, [M+H]+=593, 595, Cl pattern.

Workup

  1. customThe title compound is prepared
  2. customThe crude product can be purified by column chromatography
  3. washeluting with 5% MeOH/

Sources & evidence

ORD record
ord-21eb58f58dab4c0b92c5ac7445a5ae71
Source dataset
uspto-grants-2003_08
Patent number
US06602864B1

Linked notes

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