Potassium Carbonate → 3-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-benzoic acid

HRID 1926364Notes

Reaction equation

HRID 1926364 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:11]=[N:12][C:13]([NH2:25])=[C:14]([C:16]3[S:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)[CH:15]=2)[CH:5]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O>[NH2:25][C:13]1[N:12]=[CH:11][C:10]([C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:26])=[O:2])=[CH:15][C:14]=1[C:16]1[S:17][C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67520373HCID 67520373, compound

Product 1

HCID 675203753-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-benzoic acid

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-(6-amino-5-benzothiazol-2-ylpyridin-3-yl)-benzoic acid methyl ester (0.980 g, 2.7 mmol) in dioxane/H2O (5:1, 30 mL) was added K2CO3 (1.5 g, 11 mmol), and the mixture was heated at 50° C. for 16 h. Evaporation of the solvents and neutralization with acetic acid gave a precipitate that was filtered off and dried in vacuo to give the title compound. 1H NMR (DMSO-d6, 300 MHz): δ=7.51-7.66 (m, 3H), 7.95-8.00 (m, 2H), 8.14-8.18 (m, 4H), 8.24 (d, J=8.4 Hz, 2H), 8.29 (d, J=1.8 Hz, 1H), 8.61 (d, J=2.1 Hz, 1H). MS(ES+): m/z=348.06 (100) [MH+]. HPLC: tR=3.42 min (polar—5 min, ZQ3).

Workup

  1. customEvaporation of the solvents and neutralization with acetic acid
  2. customgave a precipitate that
  3. filtrationwas filtered off
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ec59f8d0672d4955a180e8f3552ee99f
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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