Diisopropylethylamine → HCID 58015499、化合物

HRID 219294ノート

反応式

HRID 219294 の反応式
[F:1][C:2]1[C:3]([NH:14][NH:15][C:16](=[O:30])[C@H:17]([N:19]2[CH:28]=[CH:27][C:26]3[N:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]2=[O:29])[CH3:18])=[N:4][CH:5]=[C:6]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[CH:9]=2)[CH:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.O=C1N([C@H](C)C(O)=O)C=CC2N=CC=CC1=2.FC1C(NN)=NC=C(C2ON=C(C)C=2)C=1.CCN(C(C)C)C(C)C>C(#N)C.CO>[NH4+:4].[OH-:12].[F:1][C:2]1[C:3]([NH:14][NH:15][C:16](=[O:30])[C@H:17]([N:19]2[CH:28]=[CH:27][C:26]3[N:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]2=[O:29])[CH3:18])=[N:4][CH:5]=[C:6]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[CH:9]=2)[CH:7]=1

参加物

8

反応物 4

HCID 81531DiisopropylethylamineHCID 580154861-(3-Fluoro-5-(3-methylisoxazol-5-yl)pyridin-2-yl)hydrazineHCID 67502322HCID 67502322、化合物HCID 86761583HCID 86761583、化合物

生成物 2

HCID 14923Ammonium Hydroxide収率 1%HCID 58015499HCID 58015499、化合物収率 100.5%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

(2R)—N′-(3-fluoro-5-(3-methylisoxazol-5-yl)pyridin-2-yl)-2-(5-oxo-1,6-naphthyridin-6(5H)-yl)propanehydrazide HATU (9.0 g, 24 mmol), (R)-2-(5-oxo-1,6-naphthyridin-6(5H)-yl)propanoic acid hydrochloride and 1-(3-fluoro-5-(3-methylisoxazol-5-yl)pyridin-2-yl)hydrazine (3.6 g, 17 mmol) were taken up in acetonitrile (52 ml, 0.3 M) and cooled to 0° C. DIPEA (8.2 ml, 47 mmol) was added dropwise and the reaction was allowed to stir to room temperature for 30 minutes until complete by LCMS. The crude material was concentrated onto silica gel and then purified via MPLC eluting with 100% DCM to 90% DCM:10% MeOH:1% NH4OH to yield (2R)—N′-(3-fluoro-5-(3-methylisoxazol-5-yl)pyridin-2-yl)-2-(5-oxo-1,6-naphthyridin-6(5H)-yl)propanehydrazide (4.927 g, 77% yield).

後処理

  1. concentrationThe crude material was concentrated onto silica gel
  2. custompurified via MPLC
  3. washeluting with 100% DCM to 90% DCM

出典と根拠

ORDレコード
ord-78f6f24d866d479dba320120ada07ff6
出典データセット
uspto-grants-2012_06
特許番号
US08198448B2

反応ノート

読み込み中…