Morpholine → HCID 67167581, compound

HRID 536075Notes

Reaction equation

HRID 536075 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([NH:16][C:17]3[CH:18]=[C:19]([S:26]([NH:29][CH3:30])(=[O:28])=[O:27])[CH:20]=[CH:21][C:22]=3[N:23]([CH3:25])[CH3:24])=[N:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>CO>[ClH:1].[CH3:24][N:23]([CH3:25])[C:22]1[CH:21]=[CH:20][C:19]([S:26]([NH:29][CH3:30])(=[O:28])=[O:27])=[CH:18][C:17]=1[NH:16][C:10]1[C:9]2[C:14](=[CH:15][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[CH:7][CH:8]=2)[N:13]=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 52934572HCID 52934572, compound

Product 1

HCID 67167581HCID 67167581, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-({7-[(3-chloropropyl)oxy]-4-quinazolinyl}amino)-4-(dimethylamino)-N-methylbenzenesulfonamide (50 mg, 0.111 mmol) and morpholine (0.048 mL, 0.556 mmol) in MeOH (1 mL) was stirred at 90° C. for 3 days before being cooled and concentrated. The residue was triturated with Et2O-EtOAc and the resulting solid was collected by filtration, washed with Et2O, and dried to give 4-(dimethylamino)-N-methyl-3-[(7-{[3-(4-morpholinyl)propyl]oxy}-4-quinazolinyl)amino]benzenesulfonamide hydrochloride (33 mg, 48%) as an off-white solid.

Workup

  1. temperaturebefore being cooled
  2. concentrationconcentrated
  3. customThe residue was triturated with Et2O-EtOAc
  4. filtrationthe resulting solid was collected by filtration
  5. washwashed with Et2O
  6. customdried

Sources & evidence

ORD record
ord-2333cddeb4e846349ab0612137badb19
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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