Diisopropylethylamine → 2-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)-amino]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl}-5-methyl-benzonitrile

HRID 657798

Reaktionsgleichung

Reaktionsgleichung von HRID 657798
Cl[C:2]1[C:3]2[CH2:11][N:10]([C:12]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:13]=3[C:14]#[N:15])[CH2:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[N:21]1[CH:22]=[CH:23][N:24]2[CH:29]=[CH:28][C:27]([CH2:30][NH2:31])=[CH:26][C:25]=12.C(N(CC)C(C)C)(C)C>C(#N)C>[N:21]1[CH:22]=[CH:23][N:24]2[CH:29]=[CH:28][C:27]([CH2:30][NH:31][C:2]3[C:3]4[CH2:11][N:10]([C:12]5[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:13]=5[C:14]#[N:15])[CH2:9][CH2:8][C:4]=4[N:5]=[CH:6][N:7]=3)=[CH:26][C:25]=12

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 55289825Imidazo(1,2-a)pyridin-7-ylmethanamineHCID 598406882-(4-Chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile

Produkt 1

HCID 250592872-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)-amino]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl}-5-methyl-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A reaction mixture of 2-(4-chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile (300 mg, 1.05 mmol) and imidazo[1,2-a]pyridin-7-ylmethanamine (400 mg, 2.31 mmol) in acetonitrile (10 mL) and N,N-diisopropylethylamine (1.0 mL, 5.7 mmol) was subjected to microwave irradiation at 185° C. for 2.5 h. The reaction mixture was concentrated and purified by semi-preparative HPLC (100×20.2 mm, C18 column; 30-60% CH3CN-water [10 mM Et2NH]) to yield a light yellow solid.

Aufarbeitung

  1. customirradiation at 185° C. for 2.5 h
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by semi-preparative HPLC (100×20.2 mm, C18 column; 30-60% CH3CN-water [10 mM Et2NH])
  4. customto yield a light yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-bedd7d22a80c4f68b38db79890b8ec3f
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076345B2

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