2-Thiophenesulfonyl chloride → HCID 67278361, compound

HRID 1696266Notes

Reaction equation

HRID 1696266 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([N:7]2[C:11]3=[C:12]4[CH:18]=[CH:17][NH:16][C:13]4=[N:14][CH:15]=[C:10]3[NH:9][C:8]2=[O:19])[CH2:2]1.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[S:25](Cl)(=[O:27])=[O:26]>>[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[S:25]([N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([N:7]2[C:11]3=[C:12]4[CH:18]=[CH:17][NH:16][C:13]4=[N:14][CH:15]=[C:10]3[NH:9][C:8]2=[O:19])[CH2:2]1)(=[O:27])=[O:26]

Participants

3

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 67278038HCID 67278038, compound

Product 1

HCID 67278361HCID 67278361, compound

Conditions

Temperature
90 °C

Procedure

A mixture of 1-piperidin-3-yl-3,6-dihydroimidazo-[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (0.030M solution in pyridine, 1.00 mL), thiophene-2-sulfonyl chloride (7.3 mg) was heated at 90° C. for 16 hours. The reaction mixture was concentrated and redissolved in N,N-dimethylformamide. PS-Trisamine (50 mg), PS-Isocyanate (50 mg) was added and the mixture agitated at ambient temperature for 6 hours then filtered. The filtrate was concentrated in vacuo and purification by preparative high performance liquid chromatography gave 1-[1-(2-thienylsulfonyl)piperidin-3-yl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (0.3 mg).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionredissolved in N,N-dimethylformamide
  3. additionPS-Trisamine (50 mg), PS-Isocyanate (50 mg) was added
  4. filtrationthen filtered
  5. concentrationThe filtrate was concentrated in vacuo and purification by preparative high performance liquid chromatography

Sources & evidence

ORD record
ord-a8a95e047a3c47a69ccc983670971e44
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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