Sodium Bicarbonate → N-{5-[4-(4-Methylpiperazin-1-yl)pyrimidin-2-ylamino]benzothiazol-2-yl}benzamide

HRID 2102826Notes

Reaction equation

HRID 2102826 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([NH:10][C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:7][C:6]=2[CH:19]=1.Cl[C:21]1[N:26]=[C:25]([N:27]2[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]2)[CH:24]=[CH:23][N:22]=1.C(=O)([O-])O.[Na+]>C(O)C.[Cl-].[Na+].O>[CH3:33][N:30]1[CH2:29][CH2:28][N:27]([C:25]2[CH:24]=[CH:23][N:22]=[C:21]([NH:1][C:2]3[CH:3]=[CH:4][C:5]4[S:9][C:8]([NH:10][C:11](=[O:18])[C:12]5[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=5)=[N:7][C:6]=4[CH:19]=3)[N:26]=2)[CH2:32][CH2:31]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 17142252-Chloro-4-(4-methylpiperazin-1-yl)pyrimidineHCID 23132485N-(5-aminobenzothiazol-2-yl)benzamide

Product 1

HCID 23132481N-{5-[4-(4-Methylpiperazin-1-yl)pyrimidin-2-ylamino]benzothiazol-2-yl}benzamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

N-{5-[4-(4-Methylpiperazin-1-yl)pyrimidin-2-ylamino]benzothiazol-2-yl}benzamide was prepared by heating a mixture of N-(5-aminobenzothiazol-2-yl)benzamide (IM 5, 50 mg, 0.186 mmol) and 2-chloro-4-(4-methylpiperazin1-yl)pyrimidine (IM 10, 40 mg, 0.186 mmol) in ethanol (3 mL) to 80° C. for 4 days. Brine (25 mL) and saturated sodium hydrogencarbonate solution (25 mL) were, added and the product was extracted with chloroform (3×40 mL) and ethyl acetate (40 mL). The combined organic phases were dried over Na2SO4 and the solvent was removed. The residue was purified by pTLC (dichloromethane:methanol=4:1) to yield a solid (44 mg, 99 μmol, 53%). LC/ESI-MS: m/z=446 [M+H]+; m/z=444 [M−H]−; Rt=2.38 min.

Workup

  1. temperatureby heating
  2. additionadded
  3. extractionthe product was extracted with chloroform (3×40 mL) and ethyl acetate (40 mL)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. customthe solvent was removed
  6. customThe residue was purified by pTLC (dichloromethane:methanol=4:1)

Sources & evidence

ORD record
ord-2edb15a5808d4169aed18cf17f6286f8
Source dataset
uspto-grants-2009_08
Patent number
US07576090B2

Reaction notes

Loading…