Reserpine → 4-Piperazin-1-yl-thieno[3,2-c]pyridine-2-sulfonic acid (4-isopropyl-phenyl)-amide hydrochloride

HRID 549283

Reaction equation

HRID 549283 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([C:14]2[S:22][C:21]3[CH:20]=[CH:19][N:18]=[C:17]([Cl:23])[C:16]=3[CH:15]=2)(=[O:13])=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].S1C2C=CC=NC=2C=C1.CO[C@@H]1[C@@H](C(OC)=O)[C@@H]2[C@@H](C[N:40]3[C@H:45](C2)[C:44]2[NH:53][C:54]4[CH:59]=C(OC)C=CC=4C=2CC3)C[C@H]1OC(C1C=C(OC)C(OC)=C(OC)C=1)=O>C(#N)C>[ClH:23].[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([C:14]2[S:22][C:21]3[CH:20]=[CH:19][N:18]=[C:17]([N:40]4[CH2:45][CH2:44][NH:53][CH2:54][CH2:59]4)[C:16]=3[CH:15]=2)(=[O:13])=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 5770ReserpineHCID 12210218ThienopyridineHCID 872902414-Chloro-thieno[3,2-c]pyridine-2-sulfonic acid (4-isopropyl-phenyl)-amide

Product 1

HCID 103438804-Piperazin-1-yl-thieno[3,2-c]pyridine-2-sulfonic acid (4-isopropyl-phenyl)-amide hydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

4-Chloro-thieno[3,2-c]pyridine-2-sulfonic acid (4-isopropyl-phenyl)-amide (0.201 mmol, 1 equiv.) was used as the thienopyridine in Method H-L. Yield: 6.9 mg HPLC: tR=3.255 (System: 5% to 50% ACN in 3 min, C8), Purity: 95%, LC/MS: tR=1.255 (System: 30% to 60% ACN in 1.5 min, Hypersil BDS), Purity: 98%. MS: 417 (M+1). 1H NMR (270 MHz, CH3OH-d4) δ ppm 1.18 (d, J=6.86 Hz, 6H) 2.83 (m, 2H) 3.52 (m, 4H) 4.00 (m, 4H) 7.14 (m, 3H) 7.75 (d, J=6.60 Hz, 1H) 8.02 (m, 1H).

Sources & evidence

ORD record
ord-491fba14137b4e7da6a8d0c8f45aaf8a
Source dataset
uspto-grants-2011_05
Patent number
US07943639B2

Linked notes

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