7,12-Dimethylbenz(a)anthracene → 6-(3-amino-2-fluoropropyl)-9-chloro[1,2,4]triazolo[3,4-a]isoquinolin-3(2H)-one

HRID 1783763

反応式

HRID 1783763 の反応式
C([NH:4][CH2:5][CH:6]([F:23])[CH2:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[C:11]2=[N:19][NH:20][C:21](=[O:22])[N:10]2[CH:9]=1)C=C.CC1C2C(=CC=CC=2)C(C)=C2C=1C=CC1C2=CC=CC=1>C(Cl)CCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:4][CH2:5][CH:6]([F:23])[CH2:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[C:11]2=[N:19][NH:20][C:21](=[O:22])[N:10]2[CH:9]=1

参加物

5

反応物 2

HCID 60017,12-Dimethylbenz(a)anthraceneHCID 575909116-[3-(allylamino)-2-fluoropropyl]-9-chloro[1,2,4]triazolo[3,4-a]isoquinolin-3(2H)-one

生成物 1

HCID 575909096-(3-amino-2-fluoropropyl)-9-chloro[1,2,4]triazolo[3,4-a]isoquinolin-3(2H)-one

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 111,2-Dichloroethane溶媒

反応条件

温度
50 °C

実験手順

6-[3-(allylamino)-2-fluoropropyl]-9-chloro[1,2,4]triazolo[3,4-a]isoquinolin-3(2H)-one (6-4)(18 mg, 0.054 mmol, 1.0 equiv) and DMBA (25.2 mg, 0.16 mmol, 3.0equiv) and tetrakis(triphenylphosphine)palladium(0) (3 mg, 2.60 μmol, 0.05 equiv) were suspended in ClCH2CH2Cl (1 mL). The resulted yellow suspension was heated at 50° C. LCMS at 5 hours showed mostly product. The crude was purified with reverse phase HPLC H2O/CH3CN gradient w/0.1% TFA present) to afford the pure product (6-5). 1H NMR (500 MHz, CD3OD) δ 8.26 (d, 1H, J=2.3 Hz), 7.88 (d, 1H, J=8.5 Hz), 7.72 (dd, 1H, J=8.5, 2.3 Hz), 7.61 (s, 1H), 5.19-4.94 (dm, 1H, J=50.0 Hz), 3.52-3.33 (m, ˜4H, overlap w/solvent peak). LRMS m/z (M+H) 295.3 found, 295.1 required.

後処理

  1. customThe crude was purified with reverse phase HPLC H2O/CH3CN gradient w/0.1% TFA present)

出典と根拠

ORDレコード
ord-2926e3e4600e447a87afe72415ea8a63
出典データセット
uspto-grants-2009_03
特許番号
US07501435B2

関連ノート

読み込み中…