Actarit → 2-(4-acetylamino-phenyl)-N-(6-amino-1-butyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-acetamide

HRID 720622

반응식

HRID 720622 반응식
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.[NH2:27][C:28]1[C:29](=[O:40])[NH:30][C:31](=[O:39])[N:32]([CH2:35][CH2:36][CH2:37][CH3:38])[C:33]=1[NH2:34]>CN(C)C=O.CN(C)C1C=CN=CC=1>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C:12]([NH:27][C:28]2[C:29](=[O:40])[NH:30][C:31](=[O:39])[N:32]([CH2:35][CH2:36][CH2:37][CH3:38])[C:33]=2[NH2:34])=[O:14])=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 2018ActaritHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10584108HCID 10584108, 화합물

생성물 1

HCID 218916952-(4-acetylamino-phenyl)-N-(6-amino-1-butyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-acetamide수율 59%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

반응 조건

온도
25 °C

실험 절차

A solution of (4-acetylamino-phenyl)-acetic acid (348 mg, 1.65 mmol) in N,N-dimethylformamide (2.5 mL) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (316 mg, 1.80 mmol). The resulting mixture was stirred at 25° C. for 20 min. At this time, the reaction was treated with 5,6-diamino-1-butyl-1H-pyrimidine-2,4-dione (300 mg, 1.5 mmol) followed by 4-dimethylaminopyridine (37 mg, 0.3 mmol). The reaction was stirred at 25° C. for 18 h. At this time, the reaction was concentrated in vacuo. The residue was diluted with water (5.0 mL) and was brought to pH=5 with a 1N aqueous hydrochloric acid solution. The resulting solid was collected by filtration, washed with water, and dried in vacuo to afford 2-(4-acetylamino-phenyl)-N-(6-amino-1-butyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-acetamide (330 mg, 59%) as a light tan solid: LR-MS for C18H23N5O4 (M+H)+ at m/z=374

후처리

  1. stirringThe reaction was stirred at 25° C. for 18 h
  2. concentrationAt this time, the reaction was concentrated in vacuo
  3. additionThe residue was diluted with water (5.0 mL)
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with water
  6. customdried in vacuo

출처 및 근거

ORD 기록
ord-d8cf9b142d7845dfa56e6df71743aad3
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07135475B2

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