Thionyl Chloride → 6-Methanesulfonamido-3,4-dihydro-1'-[2-(2-chloro-pyrid-5-yl)ethyl]-spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one

HRID 1591187Notes

Reaction equation

HRID 1591187 reaction equation
Cl.[CH3:2][S:3]([NH:6][C:7]1[CH:8]=[CH:9][C:10]2[O:20][C:14]3([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH2:13][C:12](=[O:21])[C:11]=2[CH:22]=1)(=[O:5])=[O:4].Cl.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32]Cl)=[CH:27][N:26]=1.ClC1N=CC(CC(O)=O)=CC=1.S(Cl)(Cl)=O>>[CH3:2][S:3]([NH:6][C:7]1[CH:8]=[CH:9][C:10]2[O:20][C:14]3([CH2:15][CH2:16][N:17]([CH2:32][CH2:31][C:28]4[CH:29]=[CH:30][C:25]([Cl:24])=[N:26][CH:27]=4)[CH2:18][CH2:19]3)[CH2:13][C:12](=[O:21])[C:11]=2[CH:22]=1)(=[O:4])=[O:5]

Participants

5

Reactant 4

HCID 24386Thionyl ChlorideHCID 140715712-(6-Chloropyridin-3-yl)acetic acidHCID 19045253N-(4-Oxospiro[chroman-2,4'-piperidine]-6-yl)methanesulfonamide hydrochlorideHCID 85615481HCID 85615481, compound2×

Product 1

HCID 190453726-Methanesulfonamido-3,4-dihydro-1'-[2-(2-chloro-pyrid-5-yl)ethyl]-spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one

Procedure

The title compound was prepared from 3,4-dihydro-6-methanesulfonamidospiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one hydrochloride and 2-chloro-5-chloroethylpyridine hydrochloride by a procedure analogous to that described in Example 92, Step B. [The 2-chloro-5-chloroethylpyridine hydrochloride used in this reaction was obtained by treating 6-chloropyrid-3-yl acetic acid (L. A. Carlson, Acta Pharm. Suecica, 9, 411 (1972)) with borane-tetrahydrofuran complex followed by reaction with thionyl chloride.] mp 213°-215° C. Anal. Calc'd. for C21H24ClN3O4S: C, 56.05; H, 5.38; N, 9.34. Found: C, 55.93; H, 5.41; N, 9.20.

Workup

  1. customwas obtained

Sources & evidence

ORD record
ord-98b44caf7afb47a7ae3b4ec41b84ce82
Source dataset
uspto-grants-1993_04
Patent number
US05206240

Reaction notes

Loading…