Pyridine → HCID 66621249, compound

HRID 415334Notes

Reaction equation

HRID 415334 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH3:34])[CH2:12][CH2:13][C:14]1[CH:33]=[CH:32][C:17]([C:18]([NH:20][C:21]2[C:22]([OH:31])=[C:23]([CH:28]=[CH:29][CH:30]=2)[C:24]([O:26][CH3:27])=[O:25])=O)=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]([CH3:34])[CH2:12][CH2:13][C:14]1[CH:33]=[CH:32][C:17]([C:18]2[O:31][C:22]3[C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:28][CH:29]=[CH:30][C:21]=3[N:20]=2)=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 66620870HCID 66620870, compound

Product 1

HCID 66621249HCID 66621249, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of methyl 3-(4-(2-((benzyloxycarbonyl)(methyl)amino)ethyl)benzamido)-2-hydroxybenzoate (800 mg, 1.73 mmol) in anhydrous toluene (10 mL) was added anhydrous pyridine (0.76 mL, 9.5 mmol), then thionyl chloride (0.7 ml, 9.5 mmol) was added. The mixture was heated to 110° C. for 2 h. The mixture was cooled to room temperature and poured into ice water (100 mL) carefully with vigorous stirring, then extracted with ethyl acetate (50 mL×3). The organic phase was washed with saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, and concentrated to give crude product. The crude product was purified by prep-HPLC to give methyl 2-(4-(2-((benzyloxycarbonyl)(methyl)amino)ethyl)phenyl)benzo[d]oxazole-7-carboxylate 200 mg, yield 22%). LC-MS (ESI) m/z: 445 (M+1)+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (50 mL×3)
  3. washThe organic phase was washed with saturated sodium bicarbonate solution and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto give crude product
  7. customThe crude product was purified by prep-HPLC

Sources & evidence

ORD record
ord-69c5e0feeb4940d1ad9ea602cde281c5
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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