Stannous chloride dihydrate → 3-[6-{4-[5-(Amino)pyridin-2-yl]piperazin-1-yl}-4-[4-fluorophenyl]-2-(trifluoromethyl)pyrimidin-5-yl]benzenesulfonamide

HRID 1966346Notes

Reaction equation

HRID 1966346 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[N:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[N:19]=[C:18]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)[C:17]=3[C:33]3[CH:34]=[C:35]([S:39]([NH2:42])(=[O:41])=[O:40])[CH:36]=[CH:37][CH:38]=3)[CH2:12][CH2:11]2)=[N:8][CH:9]=1)([O-])=O.O.O.[Sn](Cl)Cl.C(=O)(O)[O-].[Na+]>Cl>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[N:21]=[C:20]([C:22]([F:23])([F:24])[F:25])[N:19]=[C:18]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)[C:17]=3[C:33]3[CH:34]=[C:35]([S:39]([NH2:42])(=[O:41])=[O:40])[CH:36]=[CH:37][CH:38]=3)[CH2:12][CH2:11]2)=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 672718983-[6-{4-[5-(Nitro)pyridin-2-yl]piperazin-1-yl}-4-[4-fluorophenyl]-2-(trifluoromethyl)pyrimidin-5-yl]benzenesulfonamide

Product 1

HCID 249619553-[6-{4-[5-(Amino)pyridin-2-yl]piperazin-1-yl}-4-[4-fluorophenyl]-2-(trifluoromethyl)pyrimidin-5-yl]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

3-[6-{4-[5-(Nitro)pyridin-2-yl]piperazin-1-yl}-4-[4-fluorophenyl]-2-(trifluoromethyl)pyrimidin-5-yl]benzenesulfonamide (0.13 g, 0.22 mmol) was taken in concentrated hydrochloric acid (1.5 ml) and to this tin (II) chloride dihydrate (0.145 g, 0.65 mmol) was added and the reaction mixture was stirred for 24 hours at room temperature. Subsequently the reaction mixture was poured onto crushed ice, neutralized with sodium bicarbonate, and extracted with ethyl acetate. Evaporation of the solvent yielded the required product. 1H-NMR (DMSO-d6) δ: 3.13 (m, 4H), 3.30 (m, 4H), 4.58 (br, 2H, D2O exchangeable), 6.57-6.59 (m, 1H), 6.88 (d, 1H), 7.04-7.09 (m, 2H), 7.12-7.14 (m, 2H), 7.39 (br, 2H, D2O exchangeable), 7.41 (d, 1H), 7.50-7.55 (m, 2H), 7.73-7.77 (m, 2H); MS m/z: 574.1 (M++1).

Workup

  1. additionwas added
  2. additionSubsequently the reaction mixture was poured
  3. customonto crushed ice
  4. extractionextracted with ethyl acetate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-fbfab82d7ec6481a8f7e51796db78297
Source dataset
uspto-grants-2013_04
Patent number
US08420653B2

Reaction notes

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