1,8-Naphthyridine-4-carbaldehyde → 1-isopropyl-6-[(3S,4S)-4-methyl-1-(1,8-naphthyridin-4-ylmethyl)pyrrolidin-3-yl]-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 2424789Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2424789
[CH:1]([N:4]1[C:8]2[N:9]=[C:10]([C@H:14]3[C@H:18]([CH3:19])[CH2:17][NH:16][CH2:15]3)[NH:11][C:12](=[O:13])[C:7]=2[CH:6]=[N:5]1)([CH3:3])[CH3:2].[N:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][N:28]=2)[C:23]([CH:30]=O)=[CH:22][CH:21]=1>>[CH:1]([N:4]1[C:8]2[N:9]=[C:10]([C@H:14]3[C@H:18]([CH3:19])[CH2:17][N:16]([CH2:30][C:23]4[C:24]5[C:29](=[N:28][CH:27]=[CH:26][CH:25]=5)[N:20]=[CH:21][CH:22]=4)[CH2:15]3)[NH:11][C:12](=[O:13])[C:7]=2[CH:6]=[N:5]1)([CH3:3])[CH3:2]

Komponenten

3

Edukt 2

HCID 47383921,8-Naphthyridine-4-carbaldehydeHCID 1361284601-isopropyl-6-[(3S,4S)-4-methylpyrrolidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one

Produkt 1

HCID 1358864581-isopropyl-6-[(3S,4S)-4-methyl-1-(1,8-naphthyridin-4-ylmethyl)pyrrolidin-3-yl]-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

Versuchsvorschrift

Following the procedure for the preparation of 1-cyclopentyl-6-[(3,4-trans)-4-methyl-1-(pyridin-3-ylmethyl)pyrrolidin-3-yl]-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one but substituting 1-isopropyl-6-[(3S,4S)-4-methylpyrrolidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one and 1,8-naphthyridine-4-carbaldehyde provided the title compound. 400 MHz 1H NMR (CDCl3) δ 9.15 (dd, J=4.1, 1.7 Hz, 1H), 9.07 (d, J=4.6 Hz, 1H), 8.69 (dd, J=8.3, 1.66 Hz, 1H), 7.99 (s, 1H), 7.69-7.65 (m, 1H), 7.46 (d, J=4.6 Hz, 1H), 5.00-4.93 (m, 1H), 4.14 (s, 3H), 3.26 (t, J=8.3 Hz, 1H), 3.03 (d, J=9.5 Hz, 1H), 2.92-2.90 (m, 1H), 2.80-2.76 (m, 1H), 2.52-2.43 (m, 1H), 1.50-1.46 (m, 6H), 1.20 (d, J=6.6 Hz, 3H). MS: (M+H m/z=404.1).

Quellen und Nachweise

ORD-Eintrag
ord-6bf4c00c13154049892f30d9acebb091
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07964607B2

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