Potassium Carbonate → HCID 57961664, 화합물

HRID 541836노트

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HRID 541836 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([NH:11][C:12]2[CH:13]=[C:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:15]=[CH:16][CH:17]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.[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]([CH2:8][C:9]([NH:11][C:12]3[CH:13]=[C:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:24])[CH3:23])[CH:15]=[CH:16][CH:17]=3)=[O:10])[CH:5]=[CH:6][CH:7]=2)[C:30]([Cl:34])=[CH:29][N:28]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 57962170tert-Butyl (3-{[(3-aminophenyl)acetyl]amino}phenyl)carbamate

생성물 1

HCID 57961664HCID 57961664, 화합물수율 62.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of tert-butyl (3-{[(3-aminophenyl)acetyl]amino}phenyl)carbamate (0.31 g, 0.91 mmol) and 2,4,5-trichloropyrimidine (0.15 g, 0.82 mmol) in DMF (3 mL) was added potassium carbonate (0.14 g, 0.99 mmol). The resulting mixture was stirred overnight at rt. The reaction was quenched with sat'd NH4Cl and water. EtOAc was added and the layers separated. The aqueous was extracted with EtOAc and the combined organics were washed with water and brine then dried (MgSO4), filtered, and concentrated. The crude mixture was purified by column chromatography to give the desired product (0.25 g, 62%). LCMS for C23H23Cl2N5O3 (M-tBu+H)+: m/z=432.0, 434.0. 1H NMR (400 MHz, DMSO-d6): δ 10.12 (s, 1H), 9.54 (s, 1H), 9.32 (s, 1H), 8.35 (s, 1H), 7.93 (s, 1H), 7.78 (t, J=2.1 Hz, 1H), 7.47 (s, 1H), 7.46 (m, 1H), 7.33 (dd, J=8.7, 7.5 Hz, 1H), 7.31 (m, 1H), 7.15 (m, 1H), 7.11 (t, J=8.0 Hz, 1H), 6.98 (m, 1H).

후처리

  1. customThe reaction was quenched with sat'd NH4Cl and water
  2. additionEtOAc was added
  3. customthe layers separated
  4. extractionThe aqueous was extracted with EtOAc
  5. washthe combined organics were washed with water and brine
  6. dry with materialthen dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude mixture was purified by column chromatography

출처 및 근거

ORD 기록
ord-21db813c8bd045218096412aab4330a8
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871753B2

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