Methyl 4-[(chlorosulfonyl)methyl]oxane-4-carboxylate → 4-[4-(4-Pyridin-3-yl-phenyl)piperazine-1-sulfonylmethyl]-tetrahydropyran-4-carboxylic acid methyl ester

HRID 393694Notes

Reaction equation

HRID 393694 reaction equation
BrC1C=CC(N2CCN(S(CC(C(C)C)C(O)=O)(=O)=O)CC2)=CC=1.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]2[CH:36]=[CH:35][C:34]([N:37]3[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]3)=[CH:33][CH:32]=2)[CH:26]=1.[CH3:43][O:44][C:45]([C:47]1([CH2:53][S:54](Cl)(=[O:56])=[O:55])[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1)=[O:46]>>[CH3:43][O:44][C:45]([C:47]1([CH2:53][S:54]([N:40]2[CH2:41][CH2:42][N:37]([C:34]3[CH:33]=[CH:32][C:31]([C:27]4[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=4)=[CH:36][CH:35]=3)[CH2:38][CH2:39]2)(=[O:56])=[O:55])[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1)=[O:46]

Participants

4

Reactant 3

HCID 22228396Methyl 4-[(chlorosulfonyl)methyl]oxane-4-carboxylateHCID 226466762-[4-(4-Bromophenyl)piperazine-1-sulfonylmethyl]-3-methylbutyric acidHCID 226466841-(4-Pyridin-3-yl-phenyl)piperazine

Product 1

HCID 698951164-[4-(4-Pyridin-3-yl-phenyl)piperazine-1-sulfonylmethyl]-tetrahydropyran-4-carboxylic acid methyl esterYield 55%

Procedure

Prepared according to the method for the preparation of 2-[4-(4-bromophenyl)piperazine-1-sulfonylmethyl]-3-methyl-butyric acid tert-buryl ester, from 1-(4-pyridin-3-yl-phenyl)piperazine (0.18 g) and 4-chlorosulfonylmethyl tetrahydropyran-4-carboxylic acid methyl ester (0.23 g), to yield the title compound as a white solid (0.19 g, 55%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-51c94156a9594802afc1e3001c1330ab
Source dataset
uspto-grants-2004_10
Patent number
US06809100B2

Reaction notes

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