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 1172568노트

반응식

HRID 1172568 반응식
[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

참가 물질

5

반응물 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

생성물 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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-2bb6700c32fc45bd8b71fe59ee2df9e5
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834014B2

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