1-Methyl-1H-pyrrole-2-carbonyl chloride → N-[3-[3-[2-(2,3-dihydro-1,4-benzodioxin-6-ylamino)pyrimidin-4-yl]pyrazolo[1,5-a]pyridin-2-yl]phenyl]-1-methylpyrrole-2-carboxamide

HRID 1159878Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1159878
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]4[CH:33]=[CH:32][C:27]5[O:28][CH2:29][CH2:30][O:31][C:26]=5[CH:25]=4)[N:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:34][N:35]1[CH:39]=[CH:38][CH:37]=[C:36]1[C:40](Cl)=[O:41]>C1COCC1.C(Cl)Cl>[O:28]1[C:27]2[CH:32]=[CH:33][C:24]([NH:23][C:19]3[N:18]=[C:17]([C:16]4[C:8]([C:4]5[CH:3]=[C:2]([NH:1][C:40]([C:36]6[N:35]([CH3:34])[CH:39]=[CH:38][CH:37]=6)=[O:41])[CH:7]=[CH:6][CH:5]=5)=[N:9][N:10]5[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=45)[CH:22]=[CH:21][N:20]=3)=[CH:25][C:26]=2[O:31][CH2:30][CH2:29]1

Komponenten

5

Edukt 2

HCID 27950921-Methyl-1H-pyrrole-2-carbonyl chlorideHCID 595138174-[2-(3-Aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-pyrimidinamine

Produkt 1

HCID 44529094N-[3-[3-[2-(2,3-dihydro-1,4-benzodioxin-6-ylamino)pyrimidin-4-yl]pyrazolo[1,5-a]pyridin-2-yl]phenyl]-1-methylpyrrole-2-carboxamideAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of {4-[2-(3-amino-phenyl)-pyrazolo[1,5-a]pyridin-3-yl]-pyrimidin-2-yl}-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-amine (105 mg, 0.24 mmol) in 5 mL THF was added N-methylpyrrole carbonyl chloride (37 mg, 0.26 mmol). When TLC showed the reaction to be complete, the solution was diluted with DCM and washed with a solution of saturated NaHCO3 and with brine. The organic phase was dried over MgSO4 and concentrated. The residue was triturated with diethyl ether to give the title compound as a yellow solid (119 mg, 92%). 1H NMR (400 MHz, d6-DMSO) δ 9.90 (s, 1H), 9.80 (s, 1H), 8.87 (d, J=6.8 Hz, 1H), 8.50 (s, 1H), 8.14 (d, J=6.0 Hz, 1H), 8.05 (s, 1H), 7.88 (d, J=8.0 Hz, 1H), 7.51 (m, 1H), 7.43 (m, 1H), 7.27-7.22 (m, 2H), 7.17 (t, J=6.8 Hz, 1H), 7.05-7.04 (m, 2H), 7.00 (s, 1H), 6.81 (d, J=8.4 Hz, 1H), 6.47 (d, J=6.0 Hz, 1H), 6.08-6.07 (m, 1H), 4.22 (m, 4H), 3.85 (s, 3H) ppm. HRMS calculated C31H25N7O3 [M+H]+ 544.2097 found 544.2101.

Aufarbeitung

  1. customthe reaction
  2. washwashed with a solution of saturated NaHCO3 and with brine
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-6f5f2d5f250b44f8aca7a80ce649249a
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812022B2

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