Triethylamine → Cyclopentyl-{4-[4-(6-fluoro-pyrido[3,4-d]pyrimidin-4-ylamino)-2-methyl-phenoxy]-piperidin-1-yl}-methanone

HRID 731905Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 731905
[CH:1]1([C:6](Cl)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:9][C:10]1[N:34]=[CH:33][C:13]2[N:14]=[CH:15][N:16]=[C:17]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)=[C:21]([CH3:32])[CH:20]=3)[C:12]=2[CH:11]=1.CCN(CC)CC>C(Cl)Cl>[CH:1]1([C:6]([N:29]2[CH2:28][CH2:27][CH:26]([O:25][C:22]3[CH:23]=[CH:24][C:19]([NH:18][C:17]4[C:12]5[CH:11]=[C:10]([F:9])[N:34]=[CH:33][C:13]=5[N:14]=[CH:15][N:16]=4)=[CH:20][C:21]=3[CH3:32])[CH2:31][CH2:30]2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 78284Cyclopentanecarbonyl chlorideHCID 69051976(6-Fluoro-pyrido[3,4-d]pyrimidin-4-yl)-[3-methyl-4-(piperidin-4-yloxy)-phenyl]-amine

Produkt 1

HCID 69051928Cyclopentyl-{4-[4-(6-fluoro-pyrido[3,4-d]pyrimidin-4-ylamino)-2-methyl-phenoxy]-piperidin-1-yl}-methanoneAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Cyclopentane carbonyl chloride (0.187 g, 1.41 mmol) was added to a solution of (6-Fluoro-pyrido[3,4-d]pyrimidin-4-yl)-[3-methyl-4-(piperidin-4-yloxy)-phenyl]-amine (T) (0.50 g, 1.28 mmol) and NEt3 (0.38 g, 3.84 mmol) in CH2Cl2 (15 mL After 1 h the reaction was quenched with water, the layers were separated and the organic layer was washed with 1N NaOH and water, dried over Na2SO4, and concentrated. Purification by flash column chromatography (CH2Cl2/MeOH, 97/3) afforded the title compound as a yellow solid (0.40 g, 70%). LRMS: 450.3 (MH+); 1H NMR (DMSO-d6, 400 MHz): δ 9.90 (s, 1H), δ 8.86 (s, 1H), δ 8.58 (s, 1H), δ 8.19 (s, 1H), δ 7.54-7.56 (m, 2H), δ 7.04 (d, J=9.56 Hz, 1H) δ 4.58-4.61 (m, 1H), δ 3.70-3.72 (m, 2H), δ 3.33-3.44 (m, 2H), δ 2.93-3.008 (m, 1H), δ 2.17 (s, 3H), δ 1.46-1.94 (m, 12H).

Aufarbeitung

  1. customwas quenched with water
  2. customthe layers were separated
  3. washthe organic layer was washed with 1N NaOH and water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by flash column chromatography (CH2Cl2/MeOH, 97/3)

Quellen und Nachweise

ORD-Eintrag
ord-260bdb28b711417dbf25184766b98c68
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585869B2

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