Hydrochloric Acid → 6-Chloro-16-thia-2,4,8,15,23-pentaazatetracyclo[15.3.1.1(3,7).1(9,13)]tricosa-1(21),3(23),4,6,9(22),10,12,17,19-nonaene 16,16-dioxide

HRID 541810ノート

反応式

HRID 541810 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:20]3[C:25]([Cl:26])=[CH:24][N:23]=[C:22](Cl)[N:21]=3)[CH:14]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.Cl>COCCO.O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>[Cl:26][C:25]1[CH:24]=[N:23][C:22]2[NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[C:4]([CH:3]=3)[S:8](=[O:10])(=[O:9])[NH:11][CH2:12][C:13]3[CH:14]=[C:15]([NH:19][C:20]=1[N:21]=2)[CH:16]=[CH:17][CH:18]=3

参加物

6

反応物 2

HCID 313Hydrochloric AcidHCID 579626943-Amino-N-{3-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}benzenesulfonamide

生成物 1

HCID 579622376-Chloro-16-thia-2,4,8,15,23-pentaazatetracyclo[15.3.1.1(3,7).1(9,13)]tricosa-1(21),3(23),4,6,9(22),10,12,17,19-nonaene 16,16-dioxide

試薬・触媒・溶媒 3

HCID 80192-Methoxyethanol溶媒HCID 10340Sodium Carbonate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

To a solution of 3-amino-N-{3-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}benzenesulfonamide (38.0 mg, 0.089 mmol) in 2-methoxyethanol (0.49 mL) was added 4.0 M of hydrogen chloride in 1,4-dioxane (45 μL). The resulting mixture was heated at 150° C. in the microwave for 15 min. The mixture was diluted with Na2CO3 (aq), extracted with EtOAc three times. The combined organic layers were dried, filtered and concentrated to give the crude, which was purified by Combi-Flash column chromatography (4 g column, 0 to 50% EtOAc in Hex) to the desired product as a white powder (7 mg, 20%). LCMS for C17H14ClN5O2S (M+H)+: m/z=388.0, 390.0. 1H NMR (400 MHz, CD3OD): δ 7.62 (m, 1H), 7.54 (s, 1H), 7.28 (t, J=2.0 Hz, 1H), 7.08 (ddd, J=8.0, 2.0, 1.2 Hz, 1H), 6.78 (t, J=8.0 Hz, 1H), 6.35 (m, 1H), 6.18 (ddd, J=8.0, 1.6, 1.0 Hz, 1H), 5.98 (m, 1H), 5.82 (ddd, J=7.6, 2.0, 1.0, 1H), 4.20 (s, 2H).

後処理

  1. extractionextracted with EtOAc three times
  2. customThe combined organic layers were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude, which
  6. customwas purified by Combi-Flash column chromatography (4 g column, 0 to 50% EtOAc in Hex) to the desired product as a white powder (7 mg, 20%)

出典と根拠

ORDレコード
ord-d09e1aa625fa4b868ea34a783a8c668f
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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