2,2-Difluoro-2-(2-pyridyl)ethyl trifluoromethanesulfonate → 7-Chloro-6-(2,2-difluoro-2-pyridin-2-yl-ethylthio)-2,3,4,5-tetrahydro-1H-benzo[d]azepine Hydrochloride

HRID 2041601Notes

Reaction equation

HRID 2041601 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([S:20][C:21](=O)N(C)C)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)S(OC[C:33]([F:41])([F:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1)(=O)=O>>[ClH:19].[Cl:19][C:16]1[CH:17]=[CH:18][C:11]2[CH2:10][CH2:9][NH:8][CH2:14][CH2:13][C:12]=2[C:15]=1[S:20][CH2:21][C:33]([F:41])([F:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1

Participants

3

Reactant 2

HCID 110662242,2-Difluoro-2-(2-pyridyl)ethyl trifluoromethanesulfonateHCID 576559793-tert-butoxycarbonyl-7-chloro-6-dimethylaminocarbonylthio-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 667071837-Chloro-6-(2,2-difluoro-2-pyridin-2-yl-ethylthio)-2,3,4,5-tetrahydro-1H-benzo[d]azepine HydrochlorideYield 66%

Procedure

Example 647 may be prepared essentially as described in Example 646 using 3-tert-butoxycarbonyl-7-chloro-6-dimethylcarbamoylthio-2,3,4,5-tetrahydro-1H-benzo[d]azepine and 2,2-difluoro-2-pyridin-2-yl-ethyl trifluoromethanesulfonate (prepared by following the procedure described in J. Med. Chem. 2003, 46, 461-473) (66% yield, MS (ES+) m/z 355 (M+H)+).

Workup

  1. customExample 647 may be prepared essentially
  2. customprepared

Sources & evidence

ORD record
ord-c60a5f231a9b4f88a9cdc38c9a31426b
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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