Hydrochloric Acid → 6-Chloro-4-(3-methanesulfonyl-benzenesulfonyl)-8-piperazin-1-yl-3,4-dihydro-2h-benzo[1,4]oxazine

HRID 388280Notes

Reaction equation

HRID 388280 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]3[O:22][CH2:21][CH2:20][NH:19][C:18]=3[CH:17]=[C:16](C(C)(C)C)[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[CH3:28][S:29]([C:32]1[CH:33]=[C:34]([S:38](Cl)(=[O:40])=[O:39])[CH:35]=[CH:36][CH:37]=1)(=[O:31])=[O:30].FC(F)(F)C(O)=O.[ClH:49]>C(O)C>[Cl:49][C:16]1[CH:15]=[C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[C:23]2[O:22][CH2:21][CH2:20][N:19]([S:38]([C:34]3[CH:35]=[CH:36][CH:37]=[C:32]([S:29]([CH3:28])(=[O:31])=[O:30])[CH:33]=3)(=[O:40])=[O:39])[C:18]=2[CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 2203303-(Methylsulfonyl)benzenesulfonyl chlorideHCID 690585714-(6-Tert-butyl-3,4-dihydro-2h-benzo[1,4]oxazin-8-yl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 225572666-Chloro-4-(3-methanesulfonyl-benzenesulfonyl)-8-piperazin-1-yl-3,4-dihydro-2h-benzo[1,4]oxazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Similarly, but replacing 4-(6-chloro-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)-piperazine-1-carboxylic acid tert-butyl ester with 4-(6-tert-butyl-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)-piperazine-1-carboxylic acid tert-butyl ester, and replacing 3-methylsulfonyl-benzenesulfonyl chloride with the appropriate aryl- or heteroaryl-sulfonyl chlorides followed by de-protection using trifluoracetic acid or hot hydrogen chloride in ethanol, the following was prepared:

Workup

  1. customthe following was prepared

Sources & evidence

ORD record
ord-d89b628ce7d14b839d5120a668f41dd1
Source dataset
uspto-grants-2013_02
Patent number
US08377931B2

Reaction notes

Loading…