Hydrochloric Acid → N-(5-{7-Methoxy-6-[3-(4-methyl-piperazin-1-yl)-propoxy]-quinazolin-4-ylamino}-benzothiazol-2-yl)-benzamide

HRID 2102828Notes

Reaction equation

HRID 2102828 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[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.O1CCOCC1>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: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: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 312751,4-DioxaneHCID 231324744-Chloro-7-methoxy-6-(3-(4-methylpiperazin-1-yl)propoxy)quinazolineHCID 23132485N-(5-aminobenzothiazol-2-yl)benzamide

Product 1

HCID 53308282N-(5-{7-Methoxy-6-[3-(4-methyl-piperazin-1-yl)-propoxy]-quinazolin-4-ylamino}-benzothiazol-2-yl)-benzamide

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

N-(5-{7-Methoxy-6-[3-(4-methyl-piperazin-1-yl)-propoxy]-quinazolin-4-ylamino}-benzothiazol-2-yl)-benzamide was prepared by heating a mixture of N-(5-aminobenzothiazol-2-yl)benzamide (IM 5, 35 mg, 0.13 mmol), 4-chloro-7-methoxy-6-[3-(4-methylpiperazin-1-yl)propoxy]quinazoline (IM 8, 46 mg, 0.13 mmol) and 4 M HCl in dioxane (0.09 mL, 0.39 mmol) in n-butanol (3 mL) to 110° C. for 5 h. The HCl salt of the product precipitated. It was separated by filtration and washed twice with CH2Cl2. No ether purification was necessary (65 mg, 0.1 mmol, 93%). LC:/ESI-MS: m/z=620 [M+H]+; m/z=618 [M−H]−; Rt=2.43 min.

Workup

  1. temperatureby heating
  2. customThe HCl salt of the product precipitated
  3. customIt was separated by filtration
  4. washwashed twice with CH2Cl2
  5. customNo ether purification

Sources & evidence

ORD record
ord-b9c7021151fc4d389920ec941b59829b
Source dataset
uspto-grants-2009_08
Patent number
US07576090B2

Reaction notes

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