1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → (4-{[6-Amino-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl]-methyl}-phenyl)-carbamic acid tert-butyl ester

HRID 858038ノート

反応式

HRID 858038 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.[NH2:31][C:32]1[C:33](=[O:48])[N:34]([CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[F:47])[C:35](=[O:39])[NH:36][C:37]=1[NH2:38]>CN(C)C=O.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16](=[O:18])[NH:31][C:32]2[C:33](=[O:48])[N:34]([CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[F:47])[C:35](=[O:39])[NH:36][C:37]=2[NH2:38])=[CH:13][CH:14]=1)([CH3:2])([CH3:3])[CH3:4]

参加物

6

反応物 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 28249932-(4-((Tert-butoxycarbonyl)amino)phenyl)acetic acidHCID 587628315,6-diamino-3-(2-fluoro-benzyl)-1H-pyrimidine-2,4-dione

生成物 1

HCID 58762847(4-{[6-Amino-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl]-methyl}-phenyl)-carbamic acid tert-butyl ester収率 91%

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-tert-butoxycarbonylamino-phenyl)-acetic acid in N,N-dimethylformamide under argon at 25° C. was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. The reaction was stirred at 25° C. for 5 min. At this time, the reaction was treated with 5,6-diamino-3-(2-fluoro-benzyl)-1H-pyrimidine-2,4-dione and 4-dimethylarninopyridine. 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 (75 mL) and then acidified to pH=5 with a 1.0N aqueous hydrochloric acid solution. The resulting solid was collected by filtration, rinsed well with water and cold ether, and dried in vacuo to afford (4-{[6-amino-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl]-methyl}-phenyl)-carbamic acid tert-butyl ester (4.10 g, 91%) as a yellow solid; LRMS for C28H32FN5O5 (M+H)+ at m/z=538.

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 (75 mL)
  4. filtrationThe resulting solid was collected by filtration
  5. washrinsed well with water and cold ether
  6. customdried in vacuo

出典と根拠

ORDレコード
ord-adff79f540ff495187fa18d47a10efa3
出典データセット
uspto-grants-2006_12
特許番号
US07148229B2

反応ノート

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