Hydrochloric Acid → N-(6-{7-Methoxy-6-[3-(4-methylpiperazin-1-yl)propoxy]quinazolin-4-ylamino}-benzothiazol-2-yl)benzamide

HRID 2102821Notes

Reaction equation

HRID 2102821 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]=[C:7]([NH:9][C:10](=[O:17])[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[S:8][C:4]=2[CH:3]=1.Cl[C:21]1[C:30]2[C:25](=[CH:26][C:27]([O:42][CH3:43])=[C:28]([O:31][CH2:32][CH2:33][CH2:34][N:35]3[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]3)[CH:29]=2)[N:24]=[CH:23][N:22]=1.Cl.C(=O)([O-])O.[Na+]>C(O)CCC>[CH3:43][O:42][C:27]1[CH:26]=[C:25]2[C:30]([C:21]([NH:1][C:2]3[CH:19]=[CH:18][C:5]4[N:6]=[C:7]([NH:9][C:10](=[O:17])[C:11]5[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=5)[S:8][C:4]=4[CH:3]=3)=[N:22][CH:23]=[N:24]2)=[CH:29][C:28]=1[O:31][CH2:32][CH2:33][CH2:34][N:35]1[CH2:36][CH2:37][N:38]([CH3:41])[CH2:39][CH2:40]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 810331N-(6-amino-1,3-benzothiazol-2-yl)benzamide2×HCID 231324744-Chloro-7-methoxy-6-(3-(4-methylpiperazin-1-yl)propoxy)quinazoline

Product 1

HCID 44467679N-(6-{7-Methoxy-6-[3-(4-methylpiperazin-1-yl)propoxy]quinazolin-4-ylamino}-benzothiazol-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

N-(6-{7-Methoxy-6-[3-(4-methylpiperazin-1-yl)propoxy]quinazolin-4yl-amino}benzothiazol-2-yl)benzamide was prepared by heating a mixture of N-(6-amino-benzothiazol-2-yl)benzamide (Intermediate 2, 40 mg. 0.148 μmol), 4-chloro-7-methoxy-6-[3-(4methylpiperazin-1-yl)propoxy]quinazoline (IM 8, 52 mg, 0.148 mmol), and HCl (112 μL, 4 M solution in dioxane, 0.444 mmol) in n-butanol (6 mL) to 110° C. for 5 h. Saturated sodium hydrogencarbonate solution was added and the product was extracted with ethyl acetate. After washing with water and drying over Na2SO4, the solvent was removed. The residue was taken up in little methanol, then water was slowly added. After stirring the mixture overnight, a grey solid was obtained (39 mg, 66 μmol, 45%). LC(ESI-MS: m/z=584 [M+H]+; m/z=582 [M−H]−; Rt=2.26 min.

Workup

  1. temperatureby heating
  2. extractionthe product was extracted with ethyl acetate
  3. washAfter washing with water
  4. dry with materialdrying over Na2SO4
  5. customthe solvent was removed
  6. additionwater was slowly added
  7. customa grey solid was obtained (39 mg, 66 μmol, 45%)

Sources & evidence

ORD record
ord-03b25521725f4b7bb467a31942416312
Source dataset
uspto-grants-2009_08
Patent number
US07576090B2

Reaction notes

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