Diisopropylethylamine → N'-(3-fluoro-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-2-(5-oxo-1,6-naphthyridin-6(5H)-yl)propanehydrazide

HRID 219275

反応式

HRID 219275 の反応式
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[O:26]=[C:27]1[N:36]([CH:37]([CH3:41])[C:38]([OH:40])=O)[CH:35]=[CH:34][C:33]2[N:32]=[CH:31][CH:30]=[CH:29][C:28]1=2.[F:42][C:43]1[C:44]([NH:55][NH2:56])=[N:45][CH:46]=[C:47]([C:49]2[CH:50]=[N:51][N:52]([CH3:54])[CH:53]=2)[CH:48]=1.CCN(C(C)C)C(C)C>C(#N)C>[F:42][C:43]1[C:44]([NH:55][NH:56][C:38](=[O:40])[CH:37]([N:36]2[CH:35]=[CH:34][C:33]3[N:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:27]2=[O:26])[CH3:41])=[N:45][CH:46]=[C:47]([C:49]2[CH:50]=[N:51][N:52]([CH3:54])[CH:53]=2)[CH:48]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67502323HCID 67502323、化合物HCID 675032383-fluoro-2-hydrazinyl-5-(1-methyl-1H-pyrazol-4-yl)pyridine

生成物 1

HCID 58015525N'-(3-fluoro-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-2-(5-oxo-1,6-naphthyridin-6(5H)-yl)propanehydrazide収率 68.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

HATU (1053 mg, 2.7 mmol), 2-(5-oxo-1,6-naphthyridin-6(5H)-yl)propanoic acid hydrochloride (470 mg, 1.8 mmol) and 1-(3-fluoro-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)hydrazine (421 mg, 2 mmol) (step 1 of General Method K) were taken up in 6 mL of acetonitrile. DIPEA (967 μl, 5.5 mmol) was added and the reaction was stirred for 30 minutes, until reaction was complete. The crude material was concentrated and then purified via MPLC with a gradient 100% DCM to 90% DCM/10% MeOH/1% NH4OH) to yield N′-(3-fluoro-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-2-(5-oxo-1,6-naphthyridin-6(5H)-yl)propanehydrazide (500 mg, 67% yield).

後処理

  1. concentrationThe crude material was concentrated
  2. custompurified via MPLC with a gradient 100% DCM to 90% DCM/10% MeOH/1% NH4OH)

出典と根拠

ORDレコード
ord-ff746182ae2647459d84117ec248d280
出典データセット
uspto-grants-2012_06
特許番号
US08198448B2

関連ノート

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