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

HRID 720622

反応式

HRID 720622 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
25 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-d8cf9b142d7845dfa56e6df71743aad3
出典データセット
uspto-grants-2006_11
特許番号
US07135475B2

関連ノート

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