Cesium carbonate → 9-(4-cyclopropylpiperazin-1-yl)-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

HRID 926114

反応式

HRID 926114 の反応式
Br[C:2]1[CH:11]=[N:10][C:9]2[N:8]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C:7](=[O:21])[N:6]3[N:22]=[CH:23][N:24]=[C:5]3[C:4]=2[CH:3]=1.[CH:25]1([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH2:27][CH2:26]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:25]1([N:28]2[CH2:33][CH2:32][N:31]([C:2]3[CH:11]=[N:10][C:9]4[N:8]([CH2:12][C:13]5[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=5)[C:7](=[O:21])[N:6]5[N:22]=[CH:23][N:24]=[C:5]5[C:4]=4[CH:3]=3)[CH2:30][CH2:29]2)[CH2:27][CH2:26]1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 47420041-CyclopropylpiperazineHCID 867053859-bromo-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

生成物 1

HCID 867053889-(4-cyclopropylpiperazin-1-yl)-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one収率 36.2%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

9-Bromo-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (Example 1, 63 mg, 0.16 mmol) and 1-cyclopropylpiperazine (103 mg, 0.82 mmol) were dissolved in toluene (2 mL) and nitrogen was bubbled through the mixture while BINAP (41 mg, 0.07 mmol), Cs2CO3 (159 mg, 0.49 mmol) and Pd(OAc)2 (7 mg, 0.03 mmol) were added. The mixture was heated at 100° C. for 16 h. The reaction mixture was concentrated under a stream of nitrogen and the residue was taken up in DMF and filtered. Purification (preparative HPLC, 10-70% ACN in water) afforded the title compound (25 mg, 27%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 0.84-1.00 (m, 2H), 1.38 (d, J=3.01 Hz, 2H), 2.01 (s, 2H), 2.35-2.51 (m, 1H), 3.50 (s, 4H), 3.61 (br s, 4H), 3.76 (s, 3H), 5.70 (s, 2H), 6.82 (d, J=8.53 Hz, 2H), 7.57 (d, J=8.41 Hz, 2H), 8.07 (d, J=2.89 Hz, 1H), 8.33 (s, 1H), 8.47 (d, J=2.89 Hz, 1H). [M+H]=432.2.

後処理

  1. additionwere added
  2. concentrationThe reaction mixture was concentrated under a stream of nitrogen
  3. filtrationfiltered
  4. customPurification (preparative HPLC, 10-70% ACN in water)

出典と根拠

ORDレコード
ord-83c8a21b0d114c889a9e44d629030d32
出典データセット
uspto-grants-2016_03
特許番号
US09284335B2

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