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

HRID 541813
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HRID 541813 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[C:5]([NH:7][CH2:8][C:9]1[CH:10]=[C:11]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=[CH:13][CH:14]=1)=[O:6].[Cl:26][C:27]1[N:32]=[C:31](Cl)[C:30]([Cl:34])=[CH:29][N:28]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:26][C:27]1[N:32]=[C:31]([NH:1][C:2]2[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=2)[C:5]([NH:7][CH2:8][C:9]2[CH:10]=[C:11]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:21])[CH3:19])[CH:12]=[CH:13][CH:14]=2)=[O:6])[C:30]([Cl:34])=[CH:29][N:28]=1
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 57962529tert-Butyl (3-{[(3-aminobenzoyl)amino]methyl}phenyl)carbamate

생성물 1

HCID 57962338tert-Butyl {3-[({3-[(2,5-dichloropyrimidin-4-yl)amino]benzoyl}amino)methyl]phenyl}carbamate수율 18%

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

실험 절차

To a solution of tert-butyl (3-{[(3-aminobenzoyl)amino]methyl}phenyl)carbamate (0.60 g, 1.8 mmol) and 2,4,5-trichloropyrimidine (0.183 mL, 1.6 mmol) in DMF (4.3 mL) was added potassium carbonate (0.331 g, 2.4 mmol). The resulting mixture was stirred overnight at room temperature. The reaction was quenched with sat'd NH4Cl and water. EtOAc was added and the layers separated. The aqueous layer was extracted with EtOAc twice. The combined organics were washed with water, dried, filtered and concentrated to give the crude, which was purified by silica gel column chromatography to give the desired product (138 mg, 18%). LCMS for C23H23Cl2N5O3 (M-tBu+H)+: m/z=432.0, 434.0, 436.0. 1H NMR (400 MHz, CD3OD): δ 8.23 (s, 1H), 8.04 (t, J=2.0 Hz, 1H), 7.96 (s, 1H), 7.83 (ddd, J=8.0, 2.0, 1.2 Hz, 1H), 7.67 (ddd, J=7.6, 2.4, 1.2 Hz, 1H), 7.48 (m, 2H), 7.21 (t, J=8.0 Hz, 1H), 7.00 (d, J=7.6 Hz, 1H), 4.54 (s, 2H), 1.49 (s, 9H).

후처리

  1. customThe reaction was quenched with sat'd NH4Cl and water
  2. additionEtOAc was added
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted with EtOAc twice
  5. washThe combined organics were washed with water
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the crude, which
  10. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-8569934c533d44d5a5bdfa0309aec39a
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08871753B2

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