Sodium Hydroxide → 6-Amino-5-benzothiazol-2-yl-[3,4']bipyridinyl-2'-carboxylic acid

HRID 1926368Notes

Reaction equation

HRID 1926368 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]([C:31]1[CH:36]=[C:35]([C:37]2[CH:38]=[N:39][C:40]([NH2:52])=[C:41]([C:43]3[S:44][C:45]4[CH:51]=[CH:50][CH:49]=[CH:48][C:46]=4[N:47]=3)[CH:42]=2)[CH:34]=[CH:33][N:32]=1)=[O:30].[OH-].[Na+]>CO>[NH2:52][C:40]1[N:39]=[CH:38][C:37]([C:35]2[CH:34]=[CH:33][N:32]=[C:31]([C:29]([OH:30])=[O:28])[CH:36]=2)=[CH:42][C:41]=1[C:43]1[S:44][C:45]2[CH:51]=[CH:50][CH:49]=[CH:48][C:46]=2[N:47]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 67520373HCID 67520373, compoundHCID 675208346-Amino-5-benzothiazol-2-yl-[3,4']bipyridinyl-2'-carboxylic acid methyl ester

Product 1

HCID 675211406-Amino-5-benzothiazol-2-yl-[3,4']bipyridinyl-2'-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following the procedure for 3-(6-amino-5-benzothiazol-2-ylpyridin-3-yl)-benzoic acid methyl ester, the title compound was prepared from 6-amino-5-benzothiazol-2-yl-[3,4′]bipyridinyl-2′-carboxylic acid methyl ester (1.14 g, 3.2 mmol) and NaOH (0.48 g, 12 mmol) in MeOH (10 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-757959c76caa46e1b845345c677ef274
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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