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

HRID 1581546노트

반응식

HRID 1581546 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1fc1495d99624a14adf38380e75b9e44
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06730668B2

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