Sodium Hydroxide → HCID 24803238, compound

HRID 1851743Notes

Reaction equation

HRID 1851743 reaction equation
FC(F)(F)C(O)=O.N1(C2N=CC(C3SC4C=C(C(OCC)=O)C=CC=4N=3)=CC=2)CCNCC1.[CH3:34][O:35][C:36]1[CH:63]=[CH:62][C:39]2[N:40]=[C:41]([C:43]3[CH:44]=[CH:45][C:46]([N:49]4[CH2:54][CH2:53][N:52](C(OC(C)(C)C)=O)[CH2:51][CH2:50]4)=[N:47][CH:48]=3)[S:42][C:38]=2[CH:37]=1.[OH-].[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:34][O:35][C:36]1[CH:63]=[CH:62][C:39]2[N:40]=[C:41]([C:43]3[CH:48]=[N:47][C:46]([N:49]4[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]4)=[CH:45][CH:44]=3)[S:42][C:38]=2[CH:37]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 57553407HCID 57553407, compoundHCID 67276893HCID 67276893, compound

Product 1

HCID 24803238HCID 24803238, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Methoxy-2-(6-piperazin-1-ylpyridin-3-yl)-1,3-benzothiazole was prepared according to the method used for the preparation of ethyl 2-(6-piperazin-1-ylpyridin-3-yl)-1,3-benzothiazole-6-carboxylate trifluoroacetate, from tert-butyl 4-[5-(6-methoxy-1,3-benzothiazol-2-yl)pyridin-2-yl]piperazine-1-carboxylate (0.22 g), with the exception that sodium hydroxide was used instead of sat. sodium hydrogencarbonate after completion of the reaction, and that the product was taken up in DCM thereafter. The title compound was obtained as a solid (0.15 g) after drying and concentration. 1H NMR δ 8.71 (d, 1 H) 8.07 (dd, 1 H) 7.85 (d, 1 H) 7.66 (d, 1 H) 7.09 (dd, 1 H) 6.93 (d, 1 H) 3.84 (s, 3 H) 3.47-3.64 (m, 4 H) 2.65-2.89 (m, 4 H); MS m/z (M+H) 327.

Workup

  1. custom6-Methoxy-2-(6-piperazin-1-ylpyridin-3-yl)-1,3-benzothiazole was prepared
  2. customafter completion of the reaction

Sources & evidence

ORD record
ord-7e180a178a5741dcb12dc51f8d536571
Source dataset
uspto-grants-2015_02
Patent number
US08957215B2

Reaction notes

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