Acetic Acid → HCID 178521853、化合物

HRID 1366360ノート

反応式

HRID 1366360 の反応式
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:33]=[CH:32][C:8]([C:9]([CH:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[NH:21][C:22]([NH:24][N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:23])[C:12]2=O)=O)=[CH:7][CH:6]=1.O.[NH2:35][NH2:36].CC(O)=O>CCO>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:33]=[CH:32][C:8]([C:9]2[NH:36][N:35]=[C:12]3[C:13]4[C:18]([C:19](=[O:20])[C:11]=23)=[C:17]([NH:21][C:22]([NH:24][N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[O:23])[CH:16]=[CH:15][CH:14]=4)=[CH:7][CH:6]=1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 23513714HCID 23513714、化合物

生成物 1

HCID 178521853HCID 178521853、化合物収率 61%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a suspension of 1-{2-[4-(2-chloroethoxy)benzoyl]-1,3-dioxo-indan-4-yl}-3-morpholin-4-yl-urea (39 g, 82.6 mmol) in EtOH (425 mL) was added hydrazine monohydrate (20.7 g, 413 mmol) followed by AcOH (9.9 g, 165.3 mmol). The reaction mixture was heated at reflux for 48 h. The reaction mixture was cooled to room temp. The yellow solid was collected by filtration, rinsed with EtOH and dried under vacuum. The solid was suspended in THF (1000 mL) and 1 N HCl (500 mL) was added. The resulting suspension was stirred for 90 min. Brine (500 mL) was added and the pH was adjusted to 13 with 50% NaOH. The layers were separated and the aqueous layer was washed with THF (2×300 mL). The combined organic layers were washed with 1 N HCl/brine (1×250 mL, 1:1), then brine (1×250 mL), dried (MgSO4), and concentrated under reduced pressure. The yellow solid was triturated with Et2O then dried under vacuum to give the desired pyrazole (23.5 g, 61% yield).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 48 h
  3. filtrationThe yellow solid was collected by filtration
  4. washrinsed with EtOH
  5. customdried under vacuum
  6. addition1 N HCl (500 mL) was added
  7. additionBrine (500 mL) was added
  8. customThe layers were separated
  9. washthe aqueous layer was washed with THF (2×300 mL)
  10. washThe combined organic layers were washed with 1 N HCl/brine (1×250 mL, 1:1)
  11. dry with materialbrine (1×250 mL), dried (MgSO4)
  12. concentrationconcentrated under reduced pressure
  13. customThe yellow solid was triturated with Et2O
  14. customthen dried under vacuum

出典と根拠

ORDレコード
ord-0b772e2dafba4b328eda52f9822250f5
出典データセット
uspto-grants-2011_02
特許番号
US07893057B2

反応ノート

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