Sodium Hydroxide → Morpholine-4-carboxylic acid 1-[2-(4-fluorophenyl)acetyl]-2-(2-phenoxypyrimidine-4-carbonyl)-pyrazolidin-4-yl ester

HRID 1581546ノート

反応式

HRID 1581546 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]2[CH2:15][CH:14]([O:16][C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[O:18])[CH2:13][NH:12]2)=[O:10])=[CH:4][CH:3]=1.[O:25]([C:32]1[N:37]=[C:36]([C:38](Cl)=[O:39])[CH:35]=[CH:34][N:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[OH-].[Na+]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]2[CH2:15][CH:14]([O:16][C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[O:18])[CH2:13][N:12]2[C:38]([C:36]2[CH:35]=[CH:34][N:33]=[C:32]([O:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:37]=2)=[O:39])=[O:10])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 129701582-Phenoxypyrimidine-4-carbonyl chlorideHCID 20724737Morpholine-4-carboxylic acid 1-[2-(4-fluorophenyl)acetyl]-pyrazolidin-4-yl ester

生成物 1

HCID 20724735Morpholine-4-carboxylic acid 1-[2-(4-fluorophenyl)acetyl]-2-(2-phenoxypyrimidine-4-carbonyl)-pyrazolidin-4-yl ester収率 61%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Morpholine-4-carboxylic acid 1-[2-(4-fluorophenyl)acetyl]-pyrazolidin-4-yl ester, 41, (354 mg, 1.05 mmol) and 2-phenoxypyrimidine-4-carbonyl chloride, 18, (345 mg, 1.47 mmol) are dissolved in dichloromethane (2 mL). 1.0 N NaOH (3 mL) is added dropwise at room temperature while vigorously stirring. The reaction is allowed to proceed for 12 hours after which time additional acid chloride, 18, is added and stirring continued for 3 hours. Additional acid chloride, 18, (83 mg) is added and stirring continued for an additional 12 hours. After which time the reaction is diluted with dichloromethane (50 mL) and washed with water (50 mL). The combined organic layers are washed with NaHCO3 (sat.) (50 mL) and brine (50 mL), dried, filtered and concentrated to provide a brown oil. The crude material is purified over silica (100% ethyl acetate to 5% methyl alcohol/ethyl acetate) afford 348 mg (61% yield) of the desired product as a viscous oil.

後処理

  1. stirringstirring
  2. waitcontinued for 3 hours
  3. stirringstirring
  4. waitcontinued for an additional 12 hours
  5. washwashed with water (50 mL)
  6. washThe combined organic layers are washed with NaHCO3 (sat.) (50 mL) and brine (50 mL)
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto provide a brown oil
  11. customThe crude material is purified over silica (100% ethyl acetate to 5% methyl alcohol/ethyl acetate)

出典と根拠

ORDレコード
ord-1fc1495d99624a14adf38380e75b9e44
出典データセット
uspto-grants-2004_05
特許番号
US06730668B2

反応ノート

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