Potassium Carbonate → tert-Butyl {3-[({3-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}sulfonyl)amino]phenyl}carbamate

HRID 541827ノート

反応式

HRID 541827 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[CH2:5][S:6]([NH:9][C:10]1[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:14][CH:15]=1)(=[O:8])=[O:7].[Cl:27][C:28]1[N:33]=[C:32](Cl)[C:31]([Cl:35])=[CH:30][N:29]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:27][C:28]1[N:33]=[C:32]([NH:1][C:2]2[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=2)[CH2:5][S:6]([NH:9][C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:14][CH:15]=2)(=[O:8])=[O:7])[C:31]([Cl:35])=[CH:30][N:29]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 57961598tert-Butyl (3-{[(3-aminobenzyl)sulfonyl]amino}phenyl)carbamate

生成物 1

HCID 57962160tert-Butyl {3-[({3-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}sulfonyl)amino]phenyl}carbamate収率 95.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of tert-butyl (3-{[(3-aminobenzyl)sulfonyl]amino}phenyl)carbamate (0.64 g, 1.7 mmol) and 2,4,5-trichloropyrimidine (0.28 g, 1.5 mmol) in DMF (5 mL) was added potassium carbonate (0.26 g, 1.8 mmol). The resulting mixture was stirred overnight at room temperature. The reaction was quenched with sat'd NH4Cl and water. EtOAc was then added and the layers separated. The aqueous phase was extracted with EtOAc. The combined organics were washed with water and brine then dried (MgSO4), filtered, and concentrated to give the desired product (0.75 g, 92%). LCMS for C22H23Cl2N5O4S (M-tBu+H)+: m/z=467.9, 469.9.

後処理

  1. customThe reaction was quenched with sat'd NH4Cl and water
  2. additionEtOAc was then added
  3. customthe layers separated
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washThe combined organics were washed with water and brine
  6. dry with materialthen dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-a4755c17ef374321a1a0a4c6d60b0867
出典データセット
uspto-grants-2014_10
特許番号
US08871753B2

反応ノート

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