Anthranilamide → HCID 22200422, compound

HRID 238218Notes

Reaction equation

HRID 238218 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19](O)=[O:20])[CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=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.[C:55]([NH2:64])(=[O:63])[C:56]1[C:57](=[CH:59][CH:60]=[CH:61][CH:62]=1)[NH2:58]>ClCCl.CC#N>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]2[CH2:13][CH2:14][N:15]([CH2:18][C:19]([NH:58][C:57]3[CH:59]=[CH:60][CH:61]=[CH:62][C:56]=3[C:55]([NH2:64])=[O:63])=[O:20])[CH2:16][CH2:17]2)(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 6942AnthranilamideHCID 81531DiisopropylethylamineHCID 4741928HCID 4741928, compoundHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 22200422HCID 22200422, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of [4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-acetic acid (1.10 g, 3.5 mmol), HATU (1.33 g, 3.5 mmol) and DIEA (1.22 mL, 7 mmol) in dichloromethane (40 mL) was added anthranilamide (714 mg, 5.25 mmol). The reaction was stirred at room temperature for 1 hour and then the reaction mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (50-100% ethyl acetate-hexanes) to yield the pure product. (1.18 g, 78%). 1H NMR (400 MHz, CDCl3) δ 11.82 (s, 1H), 8.66 (d, J=8.0 Hz, 1H), 7.77 (d, J=7.0 Hz, 2H), 7.51 (m, 2H), 7.11 (t, J=7.6 Hz, 1H), 7.05 (d, J=7.1 Hz, 2H), 6.10 (br s, 1H), 5.51 (br s, 1H), 3.92 (s, 3H), 3.24 (m, 6H), 2.76 (t, J=4.7 Hz, 4H); HPLC ret. time 2.46 min, 10-99% CH3CN, 5 min run; ESI-MS m/z 433.1 (M+1)+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography (50-100% ethyl acetate-hexanes)
  6. customto yield the pure product

Sources & evidence

ORD record
ord-c436b361d51e428aa347910f66449a3f
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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