Water → HCID 17858822, compound

HRID 1372784Notes

Reaction equation

HRID 1372784 reaction equation
C[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:10][C:11]2[CH:17]=[C:16]([CH2:18][C:19]([OH:21])=O)[CH:15]=[CH:14][C:12]=2[N:13]=1.[CH3:22][NH:23][CH2:24][CH2:25][O:26][C:27]1[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:28]=1.[CH3:37]CN=C=NCCCN(C)C.Cl.O>CN(C=O)C.CN(C1C=CN=CC=1)C.C1C=CC2N(O)N=NC=2C=1>[CH3:37][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:10][C:11]2[CH:17]=[C:16]([CH2:18][C:19]([N:23]([CH2:24][CH2:25][O:26][C:27]3[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:28]=3)[CH3:22])=[O:21])[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

8

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 235083152-(2-(O-tolylamino)benzo[d]oxazol-6-yl)acetic acidHCID 23512029Methyl 4-[2-(methylamino)ethoxy]benzoate

Product 1

HCID 17858822HCID 17858822, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 757711-HydroxybenzotriazoleCatalystHCID 6228DimethylformamideSolvent

Procedure

In DMF (6 ml) were dissolved 2-(2-methylphenylamino)-6-benzoxazolylacetic acid (154 mg, 0.55 mmol) and methyl 4-(2-(N-methylamino)ethoxy)benzoate (117 mg, 0.55 mmol). To the resulting solution were added EDC HCl (157 mg, 0.81 mmol), HOBt (5 mg, 0.04 mmol), and DMAP (5 mg, 0.04 mmol). The resulting mixture was stirred at room temperature for 18 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from chloroform-methanol (10:1, v/v) eluate fractions, methyl 4-(2-((2-(2-methylphenylamino)-6-benzoxazolyl)-N-methylacetamido)ethoxy)benzoate (207 mg, 80%) was obtained as a yellow oil.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by chromatography on a silica gel column, whereby from chloroform-methanol (10:1

Sources & evidence

ORD record
ord-45c2b8892105472a9791d30cbcf97cd0
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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