4-Cyanobenzenesulfonyl chloride → 4-(4-Piperazin-1-yl-pyrrolo[3,2-c]pyridine-1-sulfonyl)-benzonitrile Hydrochloride

HRID 549310Notes

Reaction equation

HRID 549310 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([Cl:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].[NH:13]1[C:21]2[CH:20]=[CH:19][N:18]=[C:17]([N:22]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]3)[C:16]=2[CH:15]=[CH:14]1>>[ClH:12].[N:22]1([C:17]2[C:16]3[CH:15]=[CH:14][N:13]([S:9]([C:6]4[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=4)(=[O:11])=[O:10])[C:21]=3[CH:20]=[CH:19][N:18]=2)[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]1

Participants

3

Reactant 2

HCID 394974-Cyanobenzenesulfonyl chlorideHCID 671567091-Piperazinecarboxylic acid,4-(1h-pyrrolo[3,2-c]pyridin-4-yl)-,1,1-dimethylethyl ester

Product 1

HCID 671568264-(4-Piperazin-1-yl-pyrrolo[3,2-c]pyridine-1-sulfonyl)-benzonitrile Hydrochloride

Procedure

4-Cyanobenzenesulfonyl chloride (26.0 mg) was added to tert-butyl 4-(1H-pyrrolo[3,2-c]pyridin-4-yl)piperazine-1-carboxylate the title compound (9.1 mg). LC/MS RT: 1.150 (System 10 till 40% MeCN over 1.5 min, ACE C8), Purity. 93%. MS: 369 (M+1) 1HNMR (CD3OD) δ ppm 3.50 (m, 4H) 4.08 (m, 4H) 7.29 (d, J=3.71 Hz, 2H) 7.98 (m, 4H) 8.29 (d, J=8.66 Hz, 2H).

Sources & evidence

ORD record
ord-b47f263b2fda4480b20c78e82443c94d
Source dataset
uspto-grants-2011_05
Patent number
US07943639B2

Reaction notes

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