Methyl 4-chloroanthranilate → HCID 11754542, compound

HRID 225772Notes

Reaction equation

HRID 225772 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[NH2:11].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.CO[C:48](=O)[C:49]1[CH:54]=[CH:53][C:52](Cl)=[CH:51][C:50]=1[NH:56][C:57]([CH:59]1[CH2:64][CH2:63][CH2:62][CH2:61][N:60]1[C:65](=[O:73])[C:66]1[CH:71]=[CH:70][C:69]([CH3:72])=[CH:68][CH:67]=1)=O>CN(C=O)C>[CH2:50]([N:56]1[C:3](=[O:12])[C:4]2[C:5](=[CH:6][C:7]([Cl:10])=[CH:8][CH:9]=2)[N:11]=[C:57]1[CH:59]1[CH2:64][CH2:63][CH2:62][CH2:61][N:60]1[C:65](=[O:73])[C:66]1[CH:71]=[CH:70][C:69]([CH3:72])=[CH:68][CH:67]=1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:48]=1

Participants

6

Reactant 4

HCID 80001Methyl 4-chloroanthranilateHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 69063202HCID 69063202, compound

Product 1

HCID 11754542HCID 11754542, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In an ice bath at −15° C., pure compound of Formula 202 (7.2 g, 29 mmol) was combined with 2-amino-4-chloro-benzoic acid methyl ester (4.5 g, 24 mmol), PyBroP (2.3 g, 4.9 mmol) and diisopropylethylamine (0.95 mL, 5.4 mmol) in DMF (30 mL). The resulting mixture was stirred ovemight, allowing the temperature to rise to room temperature with the bath. The solution was concentrated under vacuum and the residue partitioned between ethyl acetate (200 mL) and water (200 mL). The organic layer was washed with water (3×100 mL) and concentrated under vacuum. The resulting residue was purified by silica gel chromatography using 40% ethyl acetate/hexanes as eluent to give 2.66 g (21% yield) of the desired product of Formula 203, 4-chloro-2-{[1-(4-methyl-benzoyl)-piperidine-2-carbonyl]amino}-benzoic acid methyl ester, as a crystalline solid. LRMS (MH+) m/z 472.

Workup

  1. customto rise to room temperature with the bath
  2. concentrationThe solution was concentrated under vacuum
  3. customthe residue partitioned between ethyl acetate (200 mL) and water (200 mL)
  4. washThe organic layer was washed with water (3×100 mL)
  5. concentrationconcentrated under vacuum
  6. customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-54f87a778ce448d29bfe294692fd351c
Source dataset
uspto-grants-2009_07
Patent number
US07557115B2

Reaction notes

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