2-[(3E)-4-(dimethylamino)-2-oxobut-3-en-1-yl]-2,3-dihydro-1H-isoindole-1,3-dione → 7-((1,3-Dioxoisoindolin-2-yl)methyl)-2-(4-phenoxyphenyl) pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 64293

반응식

HRID 64293 반응식
C[N:2]([CH3:19])/[CH:3]=[CH:4]/[C:5](=O)[CH2:6][N:7]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=[O:17].[NH2:20][C:21]1[NH:25][N:24]=[C:23]([C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:28][CH:27]=2)[C:22]=1C#N>CC(O)=O>[O:16]=[C:15]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:17])[N:7]1[CH2:6][C:5]1[N:25]2[N:24]=[C:23]([C:26]3[CH:31]=[CH:30][C:29]([O:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[CH:28][CH:27]=3)[C:22]([C:21]#[N:20])=[C:19]2[N:2]=[CH:3][CH:4]=1

참가 물질

4

반응물 2

HCID 114368202-[(3E)-4-(dimethylamino)-2-oxobut-3-en-1-yl]-2,3-dihydro-1H-isoindole-1,3-dioneHCID 178509389HCID 178509389, 화합물

생성물 1

HCID 1176682787-((1,3-Dioxoisoindolin-2-yl)methyl)-2-(4-phenoxyphenyl) pyrazolo[1,5-a]pyrimidine-3-carbonitrile수율 40%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
120 °C

실험 절차

A mixture of (E)-2-(4-(dimethylamino)-2-oxobut-3-enyl)isoindoline-1,3-dione (600 mg, 2.33 mmol) and 5-amino-3-(4-phenoxy phenyl)-1H-pyrazole-4-carbonitrile (642 mg, 2.33 mmol) in 20 mL of HOAc was stirred and heated to 120° C. for 15 hr. The mixture was concentrated and suspended in 30 mL of solvent (PE/EA=4/1). The mixture was filtered and the solid was purified by pre-TLC (DCM/EA=50/1) to give 430 mg (40%) of 7-((1,3-dioxoisoindolin-2-yl)methyl)-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile as a solid. 1H NMR (400 MHz, DMSO-d6) δ 8.74 (d, J=4.4 Hz, 1H), 8.05 (d, J=8.8 Hz, 2H), 7.96-7.90 (m, 1H), 7.88-7.85 (m, 2H), 7.50 (d, J=4.4 Hz, 1H), 7.46-7.37 (m, 2H), 7.21-7.09 (m, 5H), 5.32 (s, 2H). MS (ESI) m/e [M+1]+ 472.1.

후처리

  1. concentrationThe mixture was concentrated
  2. filtrationThe mixture was filtered
  3. customthe solid was purified by pre-TLC (DCM/EA=50/1)

출처 및 근거

ORD 기록
ord-b904d965dc9c4734a433a4ac993d9110
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447106B2

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