N'-(3-Cyano-pyridin-2-yl)-N,N-dimethyl-formamidine → N-Benzyl-4-(4-hydroxy-phenylsulfanyl)-3-(pyrido[2,3-d]pyrimidin-4-ylamino)-benzamide

HRID 605087Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 605087
[NH2:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[S:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].C([C:28]1[C:29]([N:34]=[CH:35][N:36]([CH3:38])C)=[N:30][CH:31]=[CH:32][CH:33]=1)#N.NC1C=C(C=CC=1SC1C=CC(O)=CC=1)C(NC1C=CC(Br)=CC=1)=O>>[CH2:8]([NH:7][C:5](=[O:6])[C:4]1[CH:15]=[CH:16][C:17]([S:18][C:19]2[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=2)=[C:2]([NH:1][C:38]2[C:28]3[CH:33]=[CH:32][CH:31]=[N:30][C:29]=3[N:34]=[CH:35][N:36]=2)[CH:3]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Komponenten

4

Edukt 3

HCID 66808319N'-(3-Cyano-pyridin-2-yl)-N,N-dimethyl-formamidine2×HCID 670400893-Amino-N-benzyl-4-(4-hydroxy-phenylsulfanyl)-benzamide2×HCID 670402693-Amino-N-(4-bromo-phenyl)-4-(4-hydroxy-phenylsulfanyl)-benzamide

Produkt 1

HCID 67040819N-Benzyl-4-(4-hydroxy-phenylsulfanyl)-3-(pyrido[2,3-d]pyrimidin-4-ylamino)-benzamideAusbeute 55 %

Versuchsvorschrift

The product of Example 35A was reacted with the product of Example 29A using the procedure of Example 22C substituting the product of Example 35A for the product of Example 22B and substituting the product of Example 29A for the product of Example 8E to provide the crude title compound which was purified by column chromatography on silica gel using methanol/dichloromethane as eluent to provide the title product (39 mg, 55%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 4.45 (d, J=5.88 Hz, 2 H) 6.83 (d, J=8.82 Hz, 2 H) 6.82-6.93 (m, 1 H) 7.16-7.44 (m, 7 H) 7.56-7.81 (m, 2 H) 7.90 (br s, 1 H) 8.61 (br s, 1 H) 8.79-9.22 (br m, 3 H) 9.94 (br s, 1 H) 10.28 (br s, 1 H); MS (ESI+) m/z 480 (M+H)+.

Aufarbeitung

  1. customto provide the crude title compound which
  2. customwas purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-2ea7d70f16d6405699c41c8ed68f36a0
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910595B2

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