Hydrochloric Acid → HCID 67101658, compound

HRID 2079642Notes

Reaction equation

HRID 2079642 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[N:7][C:8](Cl)=[N:9]2)=[CH:4][CH:3]=1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH:23][CH2:24][CH2:25][CH2:26][N:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)(=[O:22])=[O:21])=[CH:16][CH:15]=1.Cl.O1CCOCC1>C(O)(C)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[N:7][C:8]([NH:13][C:14]3[CH:15]=[CH:16][C:17]([S:20]([NH:23][CH2:24][CH2:25][CH2:26][N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)(=[O:22])=[O:21])=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 457900527-Bromo-2-chloroquinazolineHCID 55137112HCID 55137112, compound

Product 1

HCID 67101658HCID 67101658, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a 0.1M suspension of 7-bromo-2-chloroquinazoline in isopropanol was added 4-amino-N-(3-(pyrrolidin-1-yl)propyl)benzenesulfonamide (1.1 eq), followed by the addition of 4.0M HCl in dioxane (1.1 eq). The reaction mixture was heated to 120° C. in an oil bath for 1 h. LCMS showed that reaction was complete under the condition. Ethyl acetate was added to the reaction flask and the mixture was washed with saturated sodium bicarbonate, brine, dried over sodium sulfate and concentrated. Desired product was a yellow color solid. ES/MS m/z 490/492 (MH+).

Workup

  1. customLCMS showed that reaction
  2. washthe mixture was washed with saturated sodium bicarbonate, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9f14fbc028ca48d58af18d18daca00cf
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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