1-Methylimidazole → 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(2-(pyridin-4-yl)ethyl)piperidine-4-carboxamide

HRID 1410032Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1410032
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:29]=[CH:28][S:27][C:14]=3[N:15]=[C:16]([N:18]3[CH2:23][CH2:22][CH:21]([C:24](O)=[O:25])[CH2:20][CH2:19]3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[N:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][NH2:38])=[CH:32][CH:31]=1.CCN=C=NCCCN(C)C.CN1C=CN=C1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:29]=[CH:28][S:27][C:14]=3[N:15]=[C:16]([N:18]3[CH2:23][CH2:22][CH:21]([C:24]([NH:38][CH2:37][CH2:36][C:33]4[CH:34]=[CH:35][N:30]=[CH:31][CH:32]=4)=[O:25])[CH2:20][CH2:19]3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Komponenten

6

Edukt 4

HCID 13901-MethylimidazoleHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 832754-PyridineethanamineHCID 683790841-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-4-carboxylic acid

Produkt 1

HCID 665489561-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(2-(pyridin-4-yl)ethyl)piperidine-4-carboxamideAusbeute 48,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The mixture of 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-4-carboxylic acid (50 mg, 0.12 mmol), 2-(pyridin-4-yl)ethanamine (22 mg, 0.18 mmol), EDCI (69 mg, 0.36 mmol) and 1-methyl-1H-imidazole (50 mg, 0.60 mmol) in 25 mL of DCM was stirred at room temperature for 16 hours. Excess of DCM was removed under reduced pressure and the residue was washed with H2O (30 mL) and EtOAc (20 mL) dried under reduced pressure to give 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(2-(pyridin-4-yl)ethyl)piperidine-4-carboxamide (30 mg, 48%) as a yellow solid. 1H NMR (300 MHz, CD3OD): δ 8.62 (s, 1H), 8.44-8.42 (m, 2H), 7.61 (d, 1H, J=2.4 Hz), 7.31-7.18 (m, 3H), 6.95 (d, 1H, J=8.7 Hz), 4.82-4.77 (m, 2H), 3.86 (s, 3H), 3.84 (s, 3H), 3.47 (t, 2H, J=6.9 Hz), 2.95-2.92 (m, 2H), 2.86 (t, 2H, J=6.9 Hz), 2.44 (brs, 1H), 1.74-1.62 (m, 4H). LC-MS: 520 [M+H]+, 260 [M/2+H]+, 518 [M−H]−, tR=1.29 min. HPLC: 97.06% at 214 nm, 97.32% at 254 nm, tR=3.47 min.

Aufarbeitung

  1. customExcess of DCM was removed under reduced pressure
  2. washthe residue was washed with H2O (30 mL) and EtOAc (20 mL)
  3. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-238ccfde4dfd4e3e985ac9a8e88f2811
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921383B2

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