Pyridine → 1,1-dimethylethyl 4-(5-{4-[3-(4-{[(dimethylamino)carbonyl]amino}phenyl)-1-methyl-1H-pyrazol-4-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl}-2-pyrimidinyl)-1-piperazinecarboxylate

HRID 29009

Reaktionsgleichung

Reaktionsgleichung von HRID 29009
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]4[NH:19][C:20]([C:22]5[CH:23]=[N:24][C:25]([N:28]6[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]6)=[N:26][CH:27]=5)=[CH:21][C:14]=34)=[CH:11][N:10]([CH3:41])[N:9]=2)=[CH:4][CH:3]=1.ClC([O:45][C:46](C)=C)=O.[N:49]1[CH:54]=CC=C[CH:50]=1>>[CH3:50][N:49]([CH3:54])[C:46]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]4[NH:19][C:20]([C:22]5[CH:27]=[N:26][C:25]([N:28]6[CH2:29][CH2:30][N:31]([C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35])[CH2:32][CH2:33]6)=[N:24][CH:23]=5)=[CH:21][C:14]=34)=[CH:11][N:10]([CH3:41])[N:9]=2)=[CH:6][CH:7]=1)=[O:45]

Komponenten

4

Edukt 3

HCID 1049PyridineHCID 93846Isopropenyl chloroformateHCID 689985601,1-dimethylethyl 4-(5-{4-[3-(4-aminophenyl)-1-methyl-1H-pyrazol-4-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl}-2-pyrimidinyl)-1-piperazinecarboxylate

Produkt 1

HCID 689990501,1-dimethylethyl 4-(5-{4-[3-(4-{[(dimethylamino)carbonyl]amino}phenyl)-1-methyl-1H-pyrazol-4-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl}-2-pyrimidinyl)-1-piperazinecarboxylateAusbeute 27 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 1,1-dimethylethyl 4-(5-{4-[3-(4-aminophenyl)-1-methyl-1H-pyrazol-4-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl}-2-pyrimidinyl)-1-piperazinecarboxylate (0.326 mmol) in pyridine (8 ml) under argon at 0° C. was added isopropenyl chloroformate (1.31 mmol) portionwise over 3 hours maintaining the reaction temperature at 0° C. The resulting solution was concentrated, purified by reverse-phase. This intermediate was dissolved in THF (10 ml) and dimethylamine (2M in THF, 20 ml) was added. After heating for 2 hours at 50° C., concentration in vacuo provided the title product (27%) as a yellow solid which was used without further purification. ESMS [M+H]+: 623.2.

Aufarbeitung

  1. concentrationThe resulting solution was concentrated
  2. custompurified by reverse-phase
  3. dissolutionThis intermediate was dissolved in THF (10 ml)
  4. additiondimethylamine (2M in THF, 20 ml) was added
  5. temperatureAfter heating for 2 hours at 50° C.
  6. concentrationconcentration in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-186d9950e3c94713a2ce7d946f82bcf6
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419988B2

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