Methanol → Pyrrolidine-1-carboxylic acid {4-[3-chloro-4-(3-phenylacetylureido)phenoxy]pyridin-2-yl}amide

HRID 492806Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 492806
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[CH:8]=2)=[CH:4][C:3]=1[Cl:23].[C:24]1([CH2:30][C:31]([N:33]=[C:34]=[O:35])=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O.CO>CN(C)C=O.FC1C=C(NC(NC(=O)CC2C=CC=CC=2)=S)C=CC=1OC1N=CN=C(NC(N2CCCC2)=O)C=1.C(OCC)(=O)C>[Cl:23][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][C:2]=1[NH:1][C:34]([NH:33][C:31](=[O:32])[CH2:30][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:35])[O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])[CH:8]=1

Komponenten

8

Edukt 4

HCID 887MethanolHCID 962WaterHCID 12259960Phenylacetyl isocyanateHCID 231535334-(4-Amino-3-chlorophenoxy)-2-[(pyrrolidin-1-yl)carbonylamino]pyridine

Produkt 1

HCID 57677481Pyrrolidine-1-carboxylic acid {4-[3-chloro-4-(3-phenylacetylureido)phenoxy]pyridin-2-yl}amideAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×HCID 11248939Pyrrolidine-1-carboxylic acid {6-[2-fluoro-4-(3-phenylacetylthioureido)phenoxy]pyrimidin-4-yl}amideLösungsmittel

Versuchsvorschrift

Pyrrolidine-1-carboxylic acid [4-(4-amino-3-chlorophenoxy)pyridin-2-yl]amide (20 mg) was dissolved in N,N-dimethylformamide (1.0 ml), and then a solution of phenylacetyl isocyanate in hexane (0.019 ml, Production Example 1) was added thereto, followed by stirring at room temperature for 1 hr. To the reaction mixture was added ethyl acetate and water to partition. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, which was then suspended in ethyl acetate:methanol=1:1. The solid was filtered off, washed with methanol, and dried under aeration to provide the titled compound (10 mg, 34%) as pale yellow powder.

Aufarbeitung

  1. customto partition
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customto give a residue, which
  6. filtrationThe solid was filtered off
  7. washwashed with methanol
  8. customdried under aeration

Quellen und Nachweise

ORD-Eintrag
ord-89c7c6fe517b4c579bf15705ba2f676f
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531532B2

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