Water → HCID 178488851, compound

HRID 496029Notes

Reaction equation

HRID 496029 reaction equation
[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]=1[C:10]1[CH:11]=[CH:12][C:13]([O:17][CH3:18])=[C:14]([NH2:16])[CH:15]=1.[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[S:24](Cl)(=[O:26])=[O:25].O>N1C=CC=CC=1>[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]=1[C:10]1[CH:11]=[CH:12][C:13]([O:17][CH3:18])=[C:14]([NH:16][S:24]([C:20]2[S:19][CH:23]=[CH:22][CH:21]=2)(=[O:26])=[O:25])[CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 855182-Thiophenesulfonyl chlorideHCID 178488849HCID 178488849, compound

Product 1

HCID 178488851HCID 178488851, compoundYield 19.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-(3H-Imidazo[4,5-b]pyridin-2-yl)-2-methoxy-phenylamine (0.5 g, 2.1 mmol prepared as described above in Chemical Example 1) was dissolved in 15 mL pyridine at room temperature. Solid thiophene 2-sulfonyl chloride (0.38 g, 2.1 mmol) was added and the resulting blood red solution was stirred overnight The reaction mixture was poured into 250 mL water, stirred for 30 minutes, and filtered to give a pink solid. The solid was recrystallized from ethyl acetate after treatment with decolorizing charcoal to give 0.16 g of thiophene-2-sulfonic acid [5-(3H-imidazo[4,5-b]pyridin-2-yl)-2-methoxy-phenyl]-amide as an off-white solid; mp 252-254° C. 1H-NMR (DMSO-d6): δ 13.26 (d, 1H), 9.85 (bs, 1H), 8.27 (m, 2H), 8.02 (m, 2H), 7.87 (d, 1H), 7.43 (d, 1H), 7.16 (m, 3H), 3.59 (s, 3H) ppm. Anal. (C17H14N4O3S2) C,H,N values were within 0.4% of theoretical values.

Workup

  1. stirringstirred for 30 minutes
  2. filtrationfiltered
  3. customto give a pink solid
  4. customThe solid was recrystallized from ethyl acetate after treatment with decolorizing charcoal

Sources & evidence

ORD record
ord-b6a2321ff7d748de800c3db1aee94be0
Source dataset
uspto-grants-2005_09
Patent number
US06943174B2

Reaction notes

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