Water → N-(2-aminophenyl)-4-((4-(pyrazin-2-yl)pyrimidin-2-ylamino)methyl)benzamide

HRID 416227Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 416227
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH2:14][C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=2)[N:8]=1.[C:24]1([NH2:31])[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[NH2:30].CCN(CC)CC.C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C.Cl>C(#N)C>[NH2:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[NH:31][C:19](=[O:21])[C:18]1[CH:17]=[CH:16][C:15]([CH2:14][NH:13][C:9]2[N:8]=[C:7]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][N:1]=3)[CH:12]=[CH:11][N:10]=2)=[CH:23][CH:22]=1

Komponenten

8

Edukt 6

HCID 962WaterHCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 666221674-[(4-Pyrazin-2-yl-pyrimidin-2-ylamino)-methyl]-benzoic acid

Produkt 1

HCID 44570891N-(2-aminophenyl)-4-((4-(pyrazin-2-yl)pyrimidin-2-ylamino)methyl)benzamideAusbeute 55,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 25a (1 g, 3.3 mmol) in dry acetonitrile (35 mL) was added 1,2-phenylenediamine (0.88 g, 8.1 mmol) followed by Et3N (2.7 mL, 19.1 mmol), HOBt.H2O (803 mg, 5.9 mmol) and EDCI.HCl (1.89 g, 9.9 mmol). The mixture was stirred at room temperature for 16 h to form a suspension which was collected by filtration, washed successively with MeCN, water and again MeCN, triturated with MeOH, filtered and dried to afford the title compound 26a (730 mg, 1.84 mmol, 55% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.57 (s, 1H), 9.43 (s, 1H), 8.75 (d, J=4.8 Hz, 2H), 8.49 (d, J=5.2 Hz, 1H), 8.11 (t, J=5.2 Hz, 1H), 7.91 (d, J=8.4 Hz, 2H), 7.59-7.37 (m, 2H), 7.44 (d, J=5.2 Hz, 1H), 7.12 (d, J=7.6 Hz, 1H), 6.94 (td, J=7.6, 1.6 Hz, 1H), 6.75 (dd, J=8.0, 1.2 Hz, 1H), 6.57 (t, J=7.2 Hz, 1H), 4.86 (s, 2H), 4.66 (d, J=5.2 Hz, 2H).

Aufarbeitung

  1. customto form a suspension which
  2. filtrationwas collected by filtration
  3. washwashed successively with MeCN, water and again MeCN
  4. customtriturated with MeOH
  5. filtrationfiltered
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-43a60525e4074b3caa6df238b2036751
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088805B2

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