1,2-Dichloroethane → N-[4-(4-{2-[1-(N,N-dimethylglycyl)-1,2,3,6-tetrahydro-4-pyridinyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}-1-ethyl-1H-pyrazol-3-yl)phenyl]-N'-phenylurea

HRID 28890

Reaktionsgleichung

Reaktionsgleichung von HRID 28890
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([C:17]4[CH2:18][CH2:19][NH:20][CH2:21][CH:22]=4)=[CH:16][C:9]=23)[C:5]([C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30]([NH:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:31])=[CH:25][CH:24]=2)=[N:4]1)[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[CH3:60][N:61]([CH3:66])[CH2:62][C:63](O)=[O:64]>CN(C)C=O.C(OCC)(=O)C>[CH3:60][N:61]([CH3:66])[CH2:62][C:63]([N:20]1[CH2:19][CH:18]=[C:17]([C:15]2[NH:14][C:10]3=[N:11][CH:12]=[CH:13][C:8]([C:6]4[C:5]([C:23]5[CH:28]=[CH:27][C:26]([NH:29][C:30]([NH:32][C:33]6[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=6)=[O:31])=[CH:25][CH:24]=5)=[N:4][N:3]([CH2:1][CH3:2])[CH:7]=4)=[C:9]3[CH:16]=2)[CH2:22][CH2:21]1)=[O:64]

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 673N,N-DimethylglycineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 58980124N-(4-{1-ethyl-4-[2-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrazol-3-yl}phenyl)-N'-phenylurea

Produkt 1

HCID 58980076N-[4-(4-{2-[1-(N,N-dimethylglycyl)-1,2,3,6-tetrahydro-4-pyridinyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}-1-ethyl-1H-pyrazol-3-yl)phenyl]-N'-phenylurea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of N-(4-{1-ethyl-4-[2-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrazol-3-yl}phenyl)-N′-phenylurea (0.23 mmol) was in N,N-dimethylformamide (3.0 mL) was added EDC (0.39 mmol), HOBt (0.39 mmol), triethylamine (1.38 mmol) followed by N,N dimethylglycine (0.39 mmol). The reaction stirred at room temp for 16 h. The reaction was poured into ethyl acetate and washed saturated sodium bicarbonate (2×10 mL). The organic layer was evaporated and purification of the residue by Gilson reverse phase HPLC provided the title product. ESMS [M+H]+: 589.4

Aufarbeitung

  1. washwashed saturated sodium bicarbonate (2×10 mL)
  2. customThe organic layer was evaporated
  3. custompurification of the residue by Gilson reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-ec8271dca1a54b659b17ee92a2b6c5ac
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419988B2

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