Hydrochloric Acid → 1,3-Dihydro-1-(3-phenylpropyl)-4-(4-fluorophenyl)-5-(4-pyridyl)-imidazol-2-one

HRID 719754노트

반응식

HRID 719754 반응식
[C:1]1([CH2:7][CH2:8][CH2:9][NH:10][C:11]([NH:13][CH:14]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[C:15](OC)(OC)[C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[OH-].[Na+]>>[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[C:15]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[C:14]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[NH:13][C:11]2=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

4

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2회HCID 21901874N-(3-phenylpropyl)-N'-[(2,2-dimethoxy-2-(4-pyridyl)-1-(4-fluorophenyl)ethyl)] urea

생성물 1

HCID 113262601,3-Dihydro-1-(3-phenylpropyl)-4-(4-fluorophenyl)-5-(4-pyridyl)-imidazol-2-one

실험 절차

N-(3-phenylpropyl)-N′-[(2,2-dimethoxy-2-(4-pyridyl)-1-(4-fluorophenyl)ethyl)] urea (224 g, 0.45 mol) was mixed with 4N HCl (800 g) and heated under reflux for 4–5 h (95–100° C.). Upon completion, the reaction was cooled to room temperature and adjusted to pH 13 with 8N NaOH solution (480 g), resulting in precipitation of a solid product. The pH of the suspension was controlled to pH≧13 for 30 min, with addition of sodium hydroxide as needed. The suspension was centrifuged and the aqueous phase removed and discarded. The solid was resuspended in 2N NaOH solution (1000 g), centrifuged a second time and then re-suspended in water (2×1000 g, water phase pH 7). The solid product was dried at 45–50° C., under vacuum (for about 4–5 days), to a final water content of <2%, to yield the product as a tan solid.

후처리

  1. temperatureheated
  2. temperatureunder reflux for 4–5 h (95–100° C.)
  3. customresulting in precipitation of a solid product
  4. customthe aqueous phase removed
  5. dry with materialThe solid product was dried at 45–50° C., under vacuum (for about 4–5 days), to a final water content of <2%

출처 및 근거

ORD 기록
ord-63378d7be1924384876fd3f0a0cb0d4d
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07132544B2

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