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

HRID 492806Notes

Reaction equation

HRID 492806 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×HCID 11248939Pyrrolidine-1-carboxylic acid {6-[2-fluoro-4-(3-phenylacetylthioureido)phenoxy]pyrimidin-4-yl}amideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-89c7c6fe517b4c579bf15705ba2f676f
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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