Thienopyridine → 4-Piperazin-1-yl-thieno[3,2-c]pyridine-2-sulfonic Acid (4-chloro-2,5-dimethoxy-phenyl)amide Hydrochloride

HRID 549286Notes

Reaction equation

HRID 549286 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]3[CH:20]=[C:21]([S:23](=[O:37])(=[O:36])[NH:24][C:25]4[CH:30]=[C:29]([O:31][CH3:32])[C:28]([Cl:33])=[CH:27][C:26]=4[O:34][CH3:35])[S:22][C:18]=3[CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.S1C2C=CC=NC=2C=C1>C(#N)C>[ClH:33].[Cl:33][C:28]1[C:29]([O:31][CH3:32])=[CH:30][C:25]([NH:24][S:23]([C:21]2[S:22][C:18]3[CH:17]=[CH:16][N:15]=[C:14]([N:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)[C:19]=3[CH:20]=2)(=[O:37])=[O:36])=[C:26]([O:34][CH3:35])[CH:27]=1

Participants

4

Reactant 2

HCID 12210218ThienopyridineHCID 671571364-[2-(4-Chloro-2,5-dimethoxy-phenylsulfamoyl)-thieno[3,2-c]pyridin-4-yl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 671563704-Piperazin-1-yl-thieno[3,2-c]pyridine-2-sulfonic Acid (4-chloro-2,5-dimethoxy-phenyl)amide Hydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The synthesis was preformed essentially as described in Method H-L from 4-[2-(4-chloro-2,5-dimethoxy-phenylsulfamoyl)-thieno[3,2-c]pyridin-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (0.112 mmol, 1 equiv.) was used as the thienopyridine in Method C. Yield: 14.7 mg. LC/MS: tR=0.610 (System: 30% to 60% ACN in 1.5 min, YMC), Purity: 92%. MS: 469 (M+1) 1H NMR (270 MHz, DMSO-d6) δ ppm 3.17 (s, 1H) 3.27 (s, 4H) 3.38 (s, 3H) 3.58 (d, J=4.22 Hz, 4H) 3.77 (s, 3H) 7.08 (s, 1H) 7.69 (d, J=5.81 Hz, 1H) 7.81 (s, 1H) 8.16 (d, J=5.81 Hz, 1H) 9.07 (s, 1H) 10.17 (s, 1H).

Sources & evidence

ORD record
ord-160e052a3e5848589b4b0d742f0c24c4
Source dataset
uspto-grants-2011_05
Patent number
US07943639B2

Reaction notes

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