N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine → N-(4-Bromo-benzyl)-4-(4-hydroxy-phenylsulfanyl)-3-(7-methyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzamide

HRID 605083Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 605083
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[S:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=1)=[O:6].C([C:29]1[C:30]([N:36]=[CH:37][N:38]([CH3:40])C)=[N:31][C:32]([CH3:35])=[CH:33][CH:34]=1)#N.NC1C=C(C=CC=1SC1C=CC(O)=CC=1)C(NC1C=CC(Br)=CC=1)=O>>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][NH:7][C:5](=[O:6])[C:4]2[CH:16]=[CH:17][C:18]([S:19][C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)=[C:2]([NH:1][C:40]3[C:29]4[CH:34]=[CH:33][C:32]([CH3:35])=[N:31][C:30]=4[N:36]=[CH:37][N:38]=3)[CH:3]=2)=[CH:10][CH:11]=1

Komponenten

4

Edukt 3

HCID 66808573N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine2×HCID 670402413-Amino-N-(4-bromo-benzyl)-4-(4-hydroxy-phenylsulfanyl)-benzamide2×HCID 670402693-Amino-N-(4-bromo-phenyl)-4-(4-hydroxy-phenylsulfanyl)-benzamide

Produkt 1

HCID 67040545N-(4-Bromo-benzyl)-4-(4-hydroxy-phenylsulfanyl)-3-(7-methyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzamideAusbeute 40 %

Versuchsvorschrift

The product of Example 33A was reacted with the product of Example 9B using the procedure of Example 22C substituting the product of Example 33A for the product of Example 22B and substituting the product of Example 9B 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 (40 mg, 40%). 1H NMR (500 MHz, DMSO-D6) δ ppm: 2.67 (s, 3 H) 4.41 (d, J=6.22 Hz, 2 H) 6.83 (d, J=8.82 Hz, 2 H) 6.86-6.95 (m, 1 H) 7.25 (d, J=8.30 Hz, 2 H) 7.28 (d, J=8.82 Hz, 2 H) 7.50 (d, J=8.30 Hz, 2 H) 7.52-7.59 (m, 1 H) 7.65-7.80 (m, 1 H) 7.81-7.98 (m, 1 H) 8.49-8.63 (m, 1 H) 8.69-8.84 (m, 1 H) 8.93-9.01 (m, 1 H) 9.83-9.97 (m, 1 H) 10.11 (s, 1 H); MS (ESI+) m/z 572/574 (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-a6b71937e84e43228692896970641e5f
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910595B2

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