N'-(3-Cyano-pyridin-2-yl)-N,N-dimethyl-formamidine → {4-[4-(3-Bromo-phenylcarbamoyl)-2-(pyrido[2,3-d]pyrimidin-4-ylamino)-phenylsulfanyl]-phenyl}-carbamic acid tert-butyl ester

HRID 605117Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 605117
[C:1]([O:5][C:6](=[O:32])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:30])[NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Br:29])[CH:24]=3)=[CH:17][C:16]=2[NH2:31])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C([C:35]1[C:36]([N:41]=[CH:42][N:43]([CH3:45])C)=[N:37][CH:38]=[CH:39][CH:40]=1)#N>>[C:1]([O:5][C:6](=[O:32])[NH:7][C:8]1[CH:9]=[CH:10][C:11]([S:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:30])[NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Br:29])[CH:24]=3)=[CH:17][C:16]=2[NH:31][C:45]2[C:35]3[CH:40]=[CH:39][CH:38]=[N:37][C:36]=3[N:41]=[CH:42][N:43]=2)=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

3

Edukt 2

HCID 66808319N'-(3-Cyano-pyridin-2-yl)-N,N-dimethyl-formamidine2×HCID 67040779{4-[2-Amino-4-(3-bromo-phenylcarbamoyl)-phenylsulfanyl]-phenyl}-carbamic acid tert-butyl ester2×

Produkt 1

HCID 67040153{4-[4-(3-Bromo-phenylcarbamoyl)-2-(pyrido[2,3-d]pyrimidin-4-ylamino)-phenylsulfanyl]-phenyl}-carbamic acid tert-butyl esterAusbeute 24 %

Versuchsvorschrift

The product of Example 64A was reacted with the product of Example 29A using the procedure of Example 13D substituting the product of Example 64A for the product of Example 13C 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 compound (31 mg, 24%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.48 (s, 9 H) 7.01 (d, J=8.46 Hz, 1 H) 7.32 (m, 4 H) 7.54 (d, J=8.46 Hz, 2 H) 7.71 (m, 2 H) 7.82 (d, J=7.72 Hz, 1 H) 8.01 (s, 1 H) 8.08 (s, 1 H) 8.64 (s, 1 H) 8.96 (d, J=8.09 Hz, 1 H) 9.11 (d, J=2.94 Hz, 1 H) 9.61 (s, 1 H) 10.35 (s, 1 H) 10.36 (s, 1 H); MS (ESI+) m/z 643/645 (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-5a9377edd6af46b0b06bca11e4580969
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910595B2

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