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

HRID 460255Notes

Reaction equation

HRID 460255 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-e56a8fc79b9744ca8777fc23c382db89
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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