Potassium Carbonate → N-{3-[(2,5-Dichloropyrimidin-4-yl)amino]benzyl}-3-nitrobenzenesulfonamide

HRID 541808ノート

反応式

HRID 541808 の反応式
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=1)[CH2:6][NH:7][S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1)(=[O:10])=[O:9].[Cl:23][C:24]1[N:29]=[C:28](Cl)[C:27]([Cl:31])=[CH:26][N:25]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:23][C:24]1[N:29]=[C:28]([NH:2][C:3]2[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=2)[CH2:6][NH:7][S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)(=[O:9])=[O:10])[C:27]([Cl:31])=[CH:26][N:25]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 66880208N-(3-Aminobenzyl)-3-nitrobenzenesulfonamide Hydrochloride

生成物 1

HCID 57961735N-{3-[(2,5-Dichloropyrimidin-4-yl)amino]benzyl}-3-nitrobenzenesulfonamide収率 28%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of N-(3-aminobenzyl)-3-nitrobenzenesulfonamide hydrochloride (0.400 g, 1.16 mmol) and 2,4,5-trichloropyrimidine (0.12 mL, 1.06 mmol) in DMF (2.8 mL) was added potassium carbonate (0.51 g, 3.7 mmol). The resulting mixture was stirred overnight at room temperature. The reaction was quenched with saturated (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 660 mg of crude residue, which was purified by Combi-Flash column chromatography (12 g column, 0 to 30% EtOAc in hexane) to give the desired product (135 mg, 28%). LCMS for C17H13Cl2N5O4S (M+H)+: m/z=453.9, 455.9, 457.9. 1H NMR (400 MHz, CD3OD): δ 8.85 (s, 1H), 8.48 (t, J=2.0 Hz, 1H), 8.29 (ddd, J=8.0, 2.0, 1.2 Hz, 1H), 8.21 (s, 1H), 8.08 (ddd, J=8.0, 1.6, 0.8 Hz, 1H), 7.64 (t, J=8.0 Hz, 1H), 7.41 (m, 2H), 7.17 (t, J=8.0 Hz, 1H), 4.21 (s, 2H).

後処理

  1. customThe reaction was quenched with saturated (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 660 mg of crude residue, which
  10. customwas purified by Combi-Flash column chromatography (12 g column, 0 to 30% EtOAc in hexane)

出典と根拠

ORDレコード
ord-13cbae393bd24d12848da69b225824ca
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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