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

HRID 541827노트

반응식

HRID 541827 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a4755c17ef374321a1a0a4c6d60b0867
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871753B2

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