Hydrochloric Acid → HCID 10090332, compound

HRID 599139Notes

Reaction equation

HRID 599139 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][N:24](C(=O)C)[CH2:23][CH2:22]4)=[CH:17][CH:16]=3)[N:9]=2)=[C:5]([CH3:7])[N:6]=1.Cl.C([O-])([O-])=O.[Na+].[Na+]>CCO>[CH3:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:16]=[CH:17][C:18]([N:21]4[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]4)=[CH:19][CH:20]=3)[N:9]=2)=[C:5]([CH3:7])[N:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 10024433HCID 10024433, compound

Product 1

HCID 10090332HCID 10090332, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(4-{4-[4-(2,4-dimethyl-thiazol-5-yl)-pyrimidin-2-ylamino]-phenyl}-piperazin-1-yl)-ethanone (0.67 g, 1.64 mmol) in EtOH (3 mL) was added 2 M aq HCl (25 mL) in a steady stream. The mixture was heated at reflux for 1 h, cooled, and basified by addition of solid Na2CO3. The product was extracted with EtOAc. The combined organics were washed with brine, dried on Na2SO4, filtered, and evaporated to afford the title compound (580 mg) as a yellow solid. 1H-NMR (CDCl3)™: 2.62 (s, 3H, CH3), 2.63 (s, 3H, CH3), 2.99 (m, 4H, CH2), 3.06 (m, 4H, CH2), 6.81 (d, 1H, J=5.4 Hz, pyrimidinyl-H), 6.89 (m, 3H, Ph-H, NH), 7.44 (m, 2H, Ph-H), 8.31 (d, 1H, J=5.4 Hz, pyrimidinyl-H). MS (ESI+) m/z 367 (C19H22N6S requires 366.5).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 h
  3. temperaturecooled
  4. extractionThe product was extracted with EtOAc
  5. washThe combined organics were washed with brine
  6. customdried on Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-abd6769832784af7927af31ada064483
Source dataset
uspto-grants-2011_03
Patent number
US07897605B2

Reaction notes

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