m-Chloroperbenzoic acid → HCID 59519015, compound

HRID 1161876Notes

Reaction equation

HRID 1161876 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[Cl:12][C:13]1[CH:14]=[C:15]([C:20]2[N:29]([CH2:30][C:31]([NH:33][CH:34]([CH3:36])[CH3:35])=[O:32])[C:28](=[O:37])[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([N:38]4[CH2:44][CH2:43][CH2:42][N:41]([CH:45]([CH3:47])[CH3:46])[CH2:40][CH2:39]4)[CH:26]=3)[N:21]=2)[CH:16]=[CH:17][C:18]=1[F:19]>C(Cl)Cl>[Cl:12][C:13]1[CH:14]=[C:15]([C:20]2[N:29]([CH2:30][C:31]([NH:33][CH:34]([CH3:35])[CH3:36])=[O:32])[C:28](=[O:37])[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([N:38]4[CH2:44][CH2:43][CH2:42][N+:41]([O-:6])([CH:45]([CH3:47])[CH3:46])[CH2:40][CH2:39]4)[CH:26]=3)[N:21]=2)[CH:16]=[CH:17][C:18]=1[F:19]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 24965093HCID 24965093, compound

Product 1

HCID 59519015HCID 59519015, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Chloroperoxybenzoic acid (19 mg, 0.078 mmol) was added to a stirred solution of 2-[2-(3-chloro-4-fluorophenyl)-6-(4-isopropylperhydro-1,4-diazepin-1-yl)-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide (EXAMPLE 6k) (40 mg, 0.078 mmol) in DCM (5 mL). The reaction mixture was stirred for 10 min at room temperature. The reaction mixture was diluted with DCM (10 mL) and washed with aqueous sodium bicarbonate solution (10 mL). The organic phase was dried (Na2SO4), concentrated under reduced pressure and purified by chromatography on silica gel with a gradient of DCM to DCM:MeOH (4:1, v/v) as eluent to afford 4-(2-(3-chloro-4-fluorophenyl)-3-(2-(isopropylamino)-2-oxoethyl)-4-oxo-3,4-dihydroquinazolin-6-yl)-1-isopropyl-1,4-diazepane 1-oxide (EXAMPLE 12a) (25 mg, 0.047 mmol, 61%).

Workup

  1. washwashed with aqueous sodium bicarbonate solution (10 mL)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. custompurified by chromatography on silica gel with a gradient of DCM to DCM:MeOH (4:1

Sources & evidence

ORD record
ord-31323a4d1e8e4eeb97d0f997bbe3c6e1
Source dataset
uspto-grants-2010_10
Patent number
US07820649B2

Reaction notes

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