5-chloro-1H-indole-3-carbaldehyde → 2-[(5-chloro-1H-indol-3-yl)methyl]-3-[4-(1-hydroxyethyl)-1-methyl-1H-pyrrol-2-yl]-7-isobutyl-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 1181816

반응식

HRID 1181816 반응식
N(C1N(CC(C)C)C(=O)N(C)C(=O)C=1)N.ClC1C=C2C(=CC=1)NC=C2C=O.C(C1C=C(C=O)N(C)C=1)(=O)C.[C:39]([C:42]1[CH:43]=[C:44]([C:48]2[N:49]([CH2:64][C:65]3[C:73]4[C:68](=[CH:69][CH:70]=[C:71]([Cl:74])[CH:72]=4)[NH:67][CH:66]=3)[N:50]=[C:51]3[C:56]=2[C:55](=[O:57])[N:54]([CH3:58])[C:53](=[O:59])[N:52]3[CH2:60][CH:61]([CH3:63])[CH3:62])[N:45]([CH3:47])[CH:46]=1)(=[O:41])[CH3:40].[BH4-].[Na+]>C1COCC1>[Cl:74][C:71]1[CH:72]=[C:73]2[C:68](=[CH:69][CH:70]=1)[NH:67][CH:66]=[C:65]2[CH2:64][N:49]1[C:48]([C:44]2[N:45]([CH3:47])[CH:46]=[C:42]([CH:39]([OH:41])[CH3:40])[CH:43]=2)=[C:56]2[C:51]([N:52]([CH2:60][CH:61]([CH3:63])[CH3:62])[C:53](=[O:59])[N:54]([CH3:58])[C:55]2=[O:57])=[N:50]1

참가 물질

7

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온도
80 °C

실험 절차

This compound was made in two steps following the procedure described above, starting with 6-hydrazino-1-isobutyl-3-methylpyrimidine-2,4(1H,3H)-dione, and condensing first 5-chloro-1H-indole-3-carbaldehyde, followed by 4-acetyl-1-methyl-1H-pyrrole-2-carbaldehyde. The isolated 3-(4-acetyl-1-methyl-1H-pyrrol-2-yl)-2-[(5-chloro-1H-indol-3-yl)methyl]-7-isobutyl-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione was treated sodium borohydride in anhydrous THF and heated at 80° C. for 1 h and the product was isolated by aqueous workup. The presence of alcohol peak (δ 64.8 ppm)was confirmed by 13C NMR (CDCl3)— no ketone peak at (δ 193.5 ppm).

후처리

  1. customthe product was isolated by aqueous workup

출처 및 근거

ORD 기록
ord-5a014ed03f864c83abe712ef853c7100
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07285558B2

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