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Potassium Carbonate → N-(3-(5-chloro-2-((4-(4-methylpiperazin-1-yl)phenyl)amino)pyrimidin-4-yl)phenyl)acrylamide

HRID 1500800
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HRID 1500800 반응식
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([NH:14][C:15](=[O:18])[CH:16]=[CH2:17])[CH:11]=[CH:12][CH:13]=2)[C:5]([Cl:19])=[CH:4][N:3]=1.[CH3:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=2)[CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:19][C:5]1[C:6]([C:8]2[CH:9]=[C:10]([NH:14][C:15](=[O:18])[CH:16]=[CH2:17])[CH:11]=[CH:12][CH:13]=2)=[N:7][C:2]([NH:31][C:30]2[CH:29]=[CH:28][C:27]([N:24]3[CH2:23][CH2:22][N:21]([CH3:20])[CH2:26][CH2:25]3)=[CH:33][CH:32]=2)=[N:3][CH:4]=1
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참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 71469246N-(3-(2,5-dichloropyrimidin-4-yl)phenyl)acrylamide

생성물 1

HCID 68042053N-(3-(5-chloro-2-((4-(4-methylpiperazin-1-yl)phenyl)amino)pyrimidin-4-yl)phenyl)acrylamide

시약·촉매·용매

2
HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

반응 조건

온도
200 °C

실험 절차

N-(3-(2,5-dichloropyrimidin-4-yl)phenyl)acrylamide (30 mg, 0.102 mmol), 4-(4-methylpiperazin-1-yl)aniline (21 mg, 0.110 mmol)) and potassium carbonate (14 mg, 0.101 mmol) were dissolved in toluene (4 mL) in a sealable microwave compatible reaction tube, then Pd2(dba)3 (2 mg, 0.002 mmol) and Xantphos (2.7 mg, 0.005 mmol) were added. The reaction tube was sealed and the reaction was heated under microwave irradiation (40 min, 200° C., 3 atm). The reaction was monitored by TLC. The product was purified by column chromatography (5% CH3OH/CH2Cl2) to give the title compound. 1H NMR (400 MHz, CD3OD): δ 8.40 (s, 1H), 8.20 (s, 1H), 7.77 (d, 1H, J=7.2 Hz), 7.59 (m, 3H), 7.46 (t, 1H, J=7.6 Hz), 6.96 (m, 2H), 6.46-6.36 (m, 2H), 5.79 (dd, 1H, J=2.4 & 9.6 Hz), 3.14 (m, 4H), 2.61 (m, 4H), 2.34 (s, 3H). ESI-MS: m/z 449.10 [M+H]+.

후처리

  1. customThe reaction tube was sealed
  2. customThe product was purified by column chromatography (5% CH3OH/CH2Cl2)

출처 및 근거

ORD 기록
ord-0effdb271b1a4642b38e7bed9d16284b
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09206176B2

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