Diphenyl Ether → 1-(4-Phenoxy-benzenesulfonyl)-4-piperazin-1-yl-1 H-pyrrolo(3,2-c)pyridine Hydrochloride

HRID 549316Notes

Reaction equation

HRID 549316 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:14](Cl)([Cl:17])(=[O:16])=[O:15].[NH:19]1[C:27]2[CH:26]=[CH:25][N:24]=[C:23]([N:28]3[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]3)[C:22]=2[CH:21]=[CH:20]1>>[ClH:17].[O:1]([C:8]1[CH:9]=[CH:10][C:11]([S:14]([N:19]2[C:27]3[CH:26]=[CH:25][N:24]=[C:23]([N:28]4[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]4)[C:22]=3[CH:21]=[CH:20]2)(=[O:16])=[O:15])=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7583Diphenyl EtherHCID 24648Sulfuryl chlorideHCID 671567091-Piperazinecarboxylic acid,4-(1h-pyrrolo[3,2-c]pyridin-4-yl)-,1,1-dimethylethyl ester

Product 1

HCID 671573191-(4-Phenoxy-benzenesulfonyl)-4-piperazin-1-yl-1 H-pyrrolo(3,2-c)pyridine Hydrochloride

Procedure

(4-Phenoxy)benzene)sulfonyl chloride (34.7 mg) was added to tert-butyl 4-(1H-pyrrolo[3,2-c]pyridin-4-yl)piperazine-1-carboxylate the title compound (12.8 mg). LC/MS RT: 1.839 (System 10 till 40% MeCN over 1.5 min, ACE C8), Purity. 95%. MS: 436 (M+1) 1HNMR (CD3OD) δ ppm 3.50 (m, J=3.96 Hz, 4H) 4.09 (m, J=4.45 Hz, 4H) 7.05 (dd, J=8.16, 6.43 Hz, 2H) 7.26 (m, 2H) 7.44 (t, J=7.79 Hz, 2H) 7.90 (m, 3H) 8.01 (d, J=3.71 Hz, 2H) 8.07 (d, J=8.91 Hz, 2H).

Sources & evidence

ORD record
ord-092aaa8a262b4f0795bdf26cb717f1e5
Source dataset
uspto-grants-2011_05
Patent number
US07943639B2

Reaction notes

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