m-Chloroperbenzoic acid → HCID 58504127, compound

HRID 2407699Notes

Reaction equation

HRID 2407699 reaction equation
ClC1C=C(C=CC=1)C(OO)=O.[NH:12]([C:19]1[C:24]([C:25]([NH2:27])=[O:26])=[CH:23][N:22]=[C:21](SC)[N:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(C(C)C)CC)(C)C.[C:39]1([C:45]2[CH:49]=[C:48]([CH2:50][N:51]3[CH2:56][CH2:55][CH:54]([CH2:57][NH2:58])[CH2:53][CH2:52]3)[O:47][N:46]=2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>ClCCl.C(OCC)(=O)C>[NH:12]([C:19]1[C:24]([C:25]([NH2:27])=[O:26])=[CH:23][N:22]=[C:21]([NH:58][CH2:57][CH:54]2[CH2:53][CH2:52][N:51]([CH2:50][C:48]3[O:47][N:46]=[C:45]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[CH:49]=3)[CH2:56][CH2:55]2)[N:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 81531DiisopropylethylamineHCID 2958214-Anilino-2-(methylthio)-5-pyrimidinecarboxamideHCID 58504252HCID 58504252, compound

Product 1

HCID 58504127HCID 58504127, compoundYield 27.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Chloroperoxybenzoic acid (195 mg) was added to a 0° C. suspension of the compound prepared in Example 93 (100 mg) in dichloromethane (4 mL). The reaction was stirred one hour at room temperature. Diisopropylethylamine (0.669 mL) and the compound prepared in Example 9 (198 mg) were added and the mixture was stirred at room temperature for 18 hours. The reaction was diluted with ethyl acetate and sequentially washed with a saturated sodium bicarbonate solution and brine. The organics were dried over magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (concentrated aqueous ammonia:methanol:ethyl acetate=0.1:0.9:25) to obtain the title compound (51 mg) having the following physical data.

Workup

  1. stirringthe mixture was stirred at room temperature for 18 hours
  2. washsequentially washed with a saturated sodium bicarbonate solution and brine
  3. dry with materialThe organics were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (concentrated aqueous ammonia:methanol:ethyl acetate=0.1:0.9:25)

Sources & evidence

ORD record
ord-2b81f81d2e8242fe8832b0d95e813af3
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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