Water → HCID 15980921, compound

HRID 1836448Notes

Reaction equation

HRID 1836448 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][N:7]=1.O=C1CCC(=O)N1[O:21][C:22](=O)[C:23]1[CH:28]=[CH:27][C:26]([N:29]=[N+:30]=[N-:31])=[CH:25][C:24]=1[OH:32].CCN(C(C)C)C(C)C.O>C(Cl)Cl.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:13])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:22](=[O:21])[C:23]2[CH:28]=[CH:27][C:26]([N:29]=[N+:30]=[N-:31])=[CH:25][C:24]=2[OH:32])=[CH:8][N:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 30356474-Azidosalicylic acid N-hydroxysuccinimide esterHCID 18619165HCID 18619165, compound

Product 1

HCID 15980921HCID 15980921, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (5-amino-pyridin-2-yloxy)-acetic acid methyl ester (40 mg, 0.19 mmol) and 4-azido-2-hydroxy-benzoic acid 2,5-dioxo-pyrrolidin-1-yl ester (50 mg, 0.192 mmol) in DCM (5 mL) was added DIPEA (66 μL, 0.38 mmol). The mixture was stirred for 15 h at an ambient temperature and was poured into water. The aqueous mixture was extracted with ethyl acetate (3×25 mL) and the combined extracts were washed with brine and dried over magnesium sulfate. Filtration and concentration gave a solid residue that was suspended in a small amount of ethyl acetate (3 mL) and was collected by filtration. This afforded 35.6 mg (54%) of (5-(4-azido-2-hydroxy-benzoylamino)-pyridin-2-yloxy)-acetic acid methyl ester: 1H NMR (300 MHz, acetone-d6) δ 11.78 (bs, 1H), 9.89 (s,1H), 7.90 (m, 1H), 7.54 (m, 2H), 6.51 (m, 1H), 6.27 (m, 1H), 6.20 (m, 1H), 4.44 (s, 2H) 3.19 (s, 3H); MS (EI) m/z 341.99 (M−H)−.

Workup

  1. extractionThe aqueous mixture was extracted with ethyl acetate (3×25 mL)
  2. washthe combined extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration and concentration
  5. customgave a solid residue that
  6. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-c08b1988d54b4650827e9d18eefc200c
Source dataset
uspto-grants-2004_08
Patent number
US06777432B1

Reaction notes

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