Diisopropylethylamine → 3-(5-{3-Methoxy-4-[3-(2-methylphenyl)ureido]-phenylacetylamino}pyrid-2-yl)-propanoic acid ethyl ester

HRID 1017992Notes

Reaction equation

HRID 1017992 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([OH:23])=O)[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])=[O:11].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[CH2:57]([O:59][C:60](=[O:70])[CH2:61][CH2:62][C:63]1[CH:68]=[CH:67][C:66]([NH2:69])=[CH:65][N:64]=1)[CH3:58]>CN(C)C=O>[CH2:57]([O:59][C:60](=[O:70])[CH2:61][CH2:62][C:63]1[CH:68]=[CH:67][C:66]([NH:69][C:21](=[O:23])[CH2:20][C:5]2[CH:6]=[CH:7][C:8]([NH:9][C:10]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:19])=[O:11])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:65][N:64]=1)[CH3:58]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 114498403-Methoxy-4-o-tolylureidophenylacetic acidHCID 23349309Ethyl 5-amino-2-pyridinepropanoate

Product 1

HCID 541518273-(5-{3-Methoxy-4-[3-(2-methylphenyl)ureido]-phenylacetylamino}pyrid-2-yl)-propanoic acid ethyl esterYield 64.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3-methoxy-4-[3-(2-methylphenyl)ureido]phenylacetic acid (0.7 g, Reference Example 31) in anhydrous dimethylformamide (25 ml) was treated sequentially with O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (0.85 g), diisopropylethylamine (0.54 g) and a solution of 3-(5-amino-pyrid-2-yl)propanoic acid ethyl ester [0.42 g, Reference Example 4(a)] in dimethylformamide (5 ml). After stirring at room temperature for 5 hours and standing over night the reaction mixture was evaporated. The residue was treated with ethyl acetate and the resulting solution was washed three times with water, then with brine and then evaporated. The residue was subjected to flash chromatography on silica gel eluting with a mixture of dichloromethane and methanol (97:3, v/v) to give the title compound (0.68 g) as a white foam.

Workup

  1. waitstanding over night
  2. customthe reaction mixture was evaporated
  3. additionThe residue was treated with ethyl acetate
  4. washthe resulting solution was washed three times with water
  5. customwith brine and then evaporated
  6. additionThe residue was subjected to flash chromatography on silica gel eluting with a mixture of dichloromethane and methanol (97:3

Sources & evidence

ORD record
ord-f4a9464f0be74e7daced5d6f7269d95a
Source dataset
uspto-grants-2002_11
Patent number
US06479519B1

Reaction notes

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