Morpholine → N-[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]-3-morpholin-4-ylpropane-1-sulfonamide

HRID 394199Notes

Reaction equation

HRID 394199 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([NH:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][N:14]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[C:15](=[O:27])[N:16]2[C:19]2[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:26])=[C:11]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[Cl:43])[CH:10]=1)(=[O:7])=[O:6].[NH:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1>C(OCC)(=O)C>[Cl:43][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=1[C:11]1[CH:10]=[C:9]([NH:8][S:5]([CH2:4][CH2:3][CH2:2][N:44]2[CH2:49][CH2:48][O:47][CH2:46][CH2:45]2)(=[O:6])=[O:7])[CH:18]=[C:17]2[C:12]=1[CH2:13][N:14]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[C:15](=[O:27])[N:16]2[C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:26]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 22647935HCID 22647935, compound

Product 1

HCID 22648174N-[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]-3-morpholin-4-ylpropane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3chloro-N-[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]propane-1-sulfonamide (93 mg, 0.14 mmol) in morpholine (0.25 mL) was heated at 130° C. for 45 min. The reaction mixture was cooled to rt, diluted with ethyl acetate, washed with water, dried (Na2SO4), and concentrated under reduced pressure. The product was purified by flash chromatography on a Biotage 40S column, eluting with 60:40 hexanes-acetone to yield N-[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]-3-morpholin-4-ylpropane-1-sulfonamide. Mass spectrum (ESI) 729 (M+1).

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe product was purified by flash chromatography on a Biotage 40S column
  5. washeluting with 60:40 hexanes-acetone

Sources & evidence

ORD record
ord-6d732f5085a642e686ea0141c7061109
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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