4-Fluorobenzaldehyde → 5-[5-(4-Fluoro-benzyl)-2,5-diaza-bicyclo[2.2.1]hept-2-yl]-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine

HRID 1172568ノート

反応式

HRID 1172568 の反応式
[CH:1]12[CH2:7][CH:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]1[N:13]=[C:12]([NH2:14])[N:11]2[N:15]=[C:16]([C:18]3[O:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[C:10]2[N:9]=1.[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][N:5]2[CH2:6][CH:1]3[CH2:7][CH:4]2[CH2:3][N:2]3[C:8]2[N:13]=[C:12]([NH2:14])[N:11]3[N:15]=[C:16]([C:18]4[O:19][CH:20]=[CH:21][CH:22]=4)[N:17]=[C:10]3[N:9]=2)=[CH:26][CH:25]=1

参加物

5

反応物 3

HCID 680234-FluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 686848935-(2,5-Diaza-bicyclo[2.2.1]hept-2-yl)-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine

生成物 1

HCID 112582655-[5-(4-Fluoro-benzyl)-2,5-diaza-bicyclo[2.2.1]hept-2-yl]-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

5-(2,5-Diaza-bicyclo[2.2.1]hept-2-yl)-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine (0.25 mmol; see Example 13(a) above) was dissolved in 4 mL of CH2Cl2 along with 1.2 eq of 4-fluorobenzaldehyde and 2 eq of sodium triacetoxyborohydride. The reaction mixture was stirred at room temperature for 18 hours. It was then concentrated and purified by preparative HPLC to afford the title compound. 1H NMR (400 Hz, DMSO-d6) δ 8.20 (brs, 1H), 7.80 (d, J=1.0 Hz, 1H), 7.00 (d, J=3.6 Hz, 1H), 7.2-7.4 (m, 4H), 6.60 (dd, J=3.6, 1.0 Hz, 1H), 6.30 (s, 1H), 4.80 (brs, 2H), 4.20-4.30 (m, 8H). MS m/z: 407 [M+H]+.

後処理

  1. concentrationIt was then concentrated
  2. custompurified by preparative HPLC

出典と根拠

ORDレコード
ord-2bb6700c32fc45bd8b71fe59ee2df9e5
出典データセット
uspto-grants-2010_11
特許番号
US07834014B2

反応ノート

読み込み中…