Sodium Carbonate → 1-[2-(4-Methoxyphenyl)thiazol-4-yl]-3-(6-piperidin-1-ylmethyl-pyridin-2-yl)urea

HRID 479702Notes

Reaction equation

HRID 479702 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[N:12]=2)=[O:9])[N:6]=1.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([C:2]2[S:3][CH:4]=[C:5]([NH:7][C:8]([NH:10][C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][N:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)[N:12]=3)=[O:9])[N:6]=2)=[CH:28][CH:27]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 187717461-(2-Bromothiazol-4-yl)-3-(6-piperidin-1-ylmethyl-pyridin-2-yl)urea

Product 1

HCID 187718521-[2-(4-Methoxyphenyl)thiazol-4-yl]-3-(6-piperidin-1-ylmethyl-pyridin-2-yl)urea

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A stirred suspension of N-(2-bromo(1,3-thiazol-4-yl)){[6-(piperidylmethyl)(2-pyridyl)]amino}carboxamide (2.23 g, 5.64 mmol), 4-methoxyphenylboronic acid (0.94 g, 6.21 mmol), PdCl2(dppf)2 (0.46 g, 0.56 mmol) and Na2CO3 (2.10 g, 17.0 mmol) in ethylene glycol dimethyl ether (25 ml) and H2O (8 ml) was heated at reflux for 12 h. After cooling to RT the mixture was filtered through Celite®. The filtrate was concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel (3:1, EtOAc:acetone) to yield the title compound as a pale yellow amorphous solid. MS m/z: 424 (M+H). Calc'd for C22H25N5O2S: 423.17.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 h
  3. filtrationwas filtered through Celite®
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe crude product was purified by flash chromatography on silica gel (3:1, EtOAc:acetone)

Sources & evidence

ORD record
ord-1f773681adfe455a8042f723462fa73c
Source dataset
uspto-grants-2003_11
Patent number
US06645990B2

Reaction notes

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