Diisopropylethylamine → HCID 58015499, 화합물

HRID 219294노트

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HRID 219294 반응식
[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

참가 물질

8

반응물 4

HCID 81531DiisopropylethylamineHCID 580154861-(3-Fluoro-5-(3-methylisoxazol-5-yl)pyridin-2-yl)hydrazineHCID 67502322HCID 67502322, 화합물HCID 86761583HCID 86761583, 화합물

생성물 2

HCID 14923Ammonium Hydroxide수율 1%HCID 58015499HCID 58015499, 화합물수율 100.5%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6342Acetonitrile용매

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온도
0 °C

실험 절차

(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).

후처리

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

출처 및 근거

ORD 기록
ord-78f6f24d866d479dba320120ada07ff6
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198448B2

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