Triethylamine → Methyl 3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)propanoate

HRID 1806116Notes

Reaction equation

HRID 1806116 reaction equation
Br[CH2:2][C:3](=O)[CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].[Br:11][C:12]1[CH:13]=[C:14]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:15]([NH:18][C:19]([NH2:21])=[S:20])=[N:16][CH:17]=1.C(N(CC)CC)C>C(O)C>[Br:11][C:12]1[CH:13]=[C:14]([O:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:15]([NH:18][C:19]2[S:20][CH:2]=[C:3]([CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7])[N:21]=2)=[N:16][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9855825Methyl 5-bromo-4-oxopentanoateHCID 866314811-(5-Bromo-3-phenoxypyridin-2-yl)thiourea

Product 1

HCID 86631509Methyl 3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)propanoateYield 80.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 5-bromo-4-oxopentanoate (2.51 g, 12.0 mmol), 1-(5-bromo-3-phenoxypyridin-2-yl)thiourea (3.00 g, 9.25 mmol), triethylamine (2.19 mL, 15.7 mmol), and ethanol (60 mL) was refluxed for 3 hours and then stirred at ambient temperature overnight. The solvent was removed to about one third original volume and partitioned between CH2Cl2 and water. The organics were concentrated and purified on silica gel eluting with 40% EtOAc/Hexanes to give the title compound (3.22 g, 80.1% yield).

Workup

  1. temperaturewas refluxed for 3 hours
  2. customThe solvent was removed to about one third original volume
  3. custompartitioned between CH2Cl2 and water
  4. concentrationThe organics were concentrated
  5. custompurified on silica gel eluting with 40% EtOAc/Hexanes

Sources & evidence

ORD record
ord-ae7b1e76afeb426d8b639346628d2782
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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