Hydrochloric Acid → N-{3-[5-(2-Chloro-4-pyrimidinyl)-2-(1-piperazinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,5-difluorobenzenesulfonamide

HRID 1961927Notes

Reaction equation

HRID 1961927 reaction equation
Cl.O1CCOCC1.[Cl:8][C:9]1[N:14]=[C:13]([C:15]2[S:19][C:18]([N:20]3[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]3)=[N:17][C:16]=2[C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([NH:39][S:40]([C:43]3[CH:48]=[C:47]([F:49])[CH:46]=[CH:45][C:44]=3[F:50])(=[O:42])=[O:41])[C:34]=2[F:51])[CH:12]=[CH:11][N:10]=1>C(Cl)Cl.CO>[Cl:8][C:9]1[N:14]=[C:13]([C:15]2[S:19][C:18]([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)=[N:17][C:16]=2[C:33]2[C:34]([F:51])=[C:35]([NH:39][S:40]([C:43]3[CH:48]=[C:47]([F:49])[CH:46]=[CH:45][C:44]=3[F:50])(=[O:42])=[O:41])[CH:36]=[CH:37][CH:38]=2)[CH:12]=[CH:11][N:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 579899561,1-Dimethylethyl 4-[5-(2-chloro-4-pyrimidinyl)-4-(3-{[(2,5-difluorophenyl)sulfonyl]amino}-2-fluorophenyl)-1,3-thiazol-2-yl]-1-piperazinecarboxylate

Product 1

HCID 57989746N-{3-[5-(2-Chloro-4-pyrimidinyl)-2-(1-piperazinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,5-difluorobenzenesulfonamideYield 130.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A 4 N solution of HCl in 1,4-dioxane (1.1 ml, 4.3 mmol) was added to a stirring solution of 1,1-dimethylethyl 4-[5-(2-chloro-4-pyrimidinyl)-4-(3-{[(2,5-difluorophenyl)sulfonyl]amino}-2-fluorophenyl)-1,3-thiazol-2-yl]-1-piperazinecarboxylate (0.36 g, 0.54 mmol) in DCM (8 mL) and MeOH (1 mL) at rt. The reaction was allowed to stir overnight. LCMS analysis indicated complete consumption of the starting material. The volatiles were removed in vacuo to afford the HCl salt of the desired product of Step C (0.40 g, 100% yield) which was carried forward without further purification. MS (ES+): 568 [M+H]+.

Workup

  1. customconsumption of the starting material
  2. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-6757fbf781fa4e20a7e340b3bb0e445d
Source dataset
uspto-grants-2013_04
Patent number
US08415345B2

Reaction notes

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