Benzoic acid, 3-amino-, methyl ester → HCID 56967243, compound

HRID 1430772Notes

Reaction equation

HRID 1430772 reaction equation
[C:1]12([C:11]3[CH:22]=[CH:21][C:14]([O:15][CH:16]=[CH:17][C:18](O)=[O:19])=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:23][O:24][C:25](=[O:33])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([NH2:32])[CH:27]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:23][O:24][C:25](=[O:33])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([NH:32][C:18](=[O:19])/[CH:17]=[CH:16]/[O:15][C:14]2[CH:13]=[CH:12][C:11]([C:1]34[CH2:10][CH:5]5[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]5)[CH2:2]3)[CH2:8]4)=[CH:22][CH:21]=2)[CH:27]=1

Participants

6

Reactant 4

HCID 78274Benzoic acid, 3-amino-, methyl esterHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 78101879HCID 78101879, compound

Product 1

HCID 56967243HCID 56967243, compoundYield 10.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(4-Adamantan-1-yl-phenoxy)-acrylic acid (110.6 mg, 0.5 mmol), 3-aminobenzoic acid methyl ester (151.2 mg, 1.0 mmol) and HATU (143.8 mg, 0.75 mmol) were mixed in 5 ml of DMF, to which DIPEA (0.13 ml, 0.75 mmol) was added, followed by stirring for 12 hours at room temperature. The reaction mixture was extracted with ethylacetate and 10% HCl, thereafter the organic layer was washed with NaCl solution and water, dried over anhydrous MgSO4, and concentrated. The residue was purified by silcagel column chromatography (n-Hexane:EtOAc=10:1) to give the target compound as a white solid (21.5 mg, yield: 10.6%).

Workup

  1. additionwas added
  2. extractionThe reaction mixture was extracted with ethylacetate and 10% HCl
  3. washthe organic layer was washed with NaCl solution and water
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silcagel column chromatography (n-Hexane:EtOAc=10:1)

Sources & evidence

ORD record
ord-37ba330925264c2696e141aa51d1a6a5
Source dataset
uspto-grants-2015_01
Patent number
US08940936B2

Reaction notes

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