Potassium Carbonate → 4-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-benzoic acid

HRID 1926366Notes

Reaction equation

HRID 1926366 reaction equation
COC(=O)C1C=CC=C(C2C=NC(N)=C(C3SC4C=CC=CC=4N=3)C=2)C=1.C[O:28][C:29](=[O:52])[C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:37]=[N:38][C:39]([NH2:51])=[C:40]([C:42]3[S:43][C:44]4[CH:50]=[CH:49][CH:48]=[CH:47][C:45]=4[N:46]=3)[CH:41]=2)=[CH:32][CH:31]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O>[NH2:51][C:39]1[N:38]=[CH:37][C:36]([C:33]2[CH:32]=[CH:31][C:30]([C:29]([OH:52])=[O:28])=[CH:35][CH:34]=2)=[CH:41][C:40]=1[C:42]1[S:43][C:44]2[CH:50]=[CH:49][CH:48]=[CH:47][C:45]=2[N:46]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67520373HCID 67520373, compoundHCID 675205364-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-benzoic acid methyl ester

Product 1

HCID 675210904-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-benzoic acid

Reagents, catalysts & solvents 1

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

Procedure

Following the procedure for 3-(6-amino-5-benzothiazol-2-ylpyridin-3-yl)-benzoic acid methyl ester, the title compound was prepared from 4-(6-amino-5-benzothiazol-2-ylpyridin-3-yl)-benzoic acid methyl ester (1.2 g, 3.3 mmol) and K2CO3 (1.5 g, 11 mmol) in dioxane/H2O (5:1, 30 mL). 1H NMR (400 MHz, DMSO-d6): δ=13.0 (very brs, 1H), 8.62 (d, J=2.2 Hz, 1H), 8.29 (d, J=2.2 Hz, 1H), 8.19-8.13 (m, 3H), 8.12 (d, J=7.8 Hz, 1H), 8.04-8.00 & 7.88-7.84 (AA′BB′, 4H), 7.57 (ddd, J=1.0, 7.0, 8.0 Hz, 1H), 7.49 (ddd, J=1.0, 7.4, 8.0 Hz, 1H). MS(ES+): m/z=348.08 (100) [MH+]. HPLC: tR=3.29 min (polar—5 min, ZQ2).

Workup

  1. customHPLC: tR=3.29 min (polar—5 min, ZQ2)

Sources & evidence

ORD record
ord-e5809146d5854d4fa885630e0f79b812
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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