Ethanol → HCID 57899007, compound

HRID 911077Notes

Reaction equation

HRID 911077 reaction equation
[Br:1][C:2]1[C:3]([CH2:22][C:23](=O)[CH2:24][C:25]([O:27]CC)=O)=[CH:4][C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:13]=2)=[N:6][CH:7]=1.C(O)C.O.[NH2:35][NH2:36]>C1COCC1>[Br:1][C:2]1[C:3]([CH2:22][C:23]2[CH2:24][C:25](=[O:27])[NH:36][N:35]=2)=[CH:4][C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:13]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 86634786HCID 86634786, compound

Product 1

HCID 57899007HCID 57899007, compoundYield 55.65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

A flask was charged with ethyl 4-(5-bromo-2-(4-phenethylthiazol-2-ylamino)pyridin-4-yl)-3-oxobutanoate (0.0500 g, 0.1024 mmol) and ethanol (2 mL), and hydrazine hydrate (0.007471 mL, 0.1536 mmol) was added. The mixture was stirred at 45° C. for 4 hours. THF (2 mL) was added, and the mixture was stirred for 18 hours at 60° C. The mixture was concentrated and the residue was triturated with 50% ethyl acetate/hexane to afford the desired product (26 mg, 55.65% yield) as a white solid. 1H NMR (d6-DMSO) δ 2.83-2.96 (m, 4H), 3.87 (s, 2H), 5.27 (s, 1H), 6.59 (s, 1H), 6.94 (s, 1H), 7.17-7.29 (m, 5H), 8.38 (s, 1H).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 18 hours at 60° C
  3. concentrationThe mixture was concentrated
  4. customthe residue was triturated with 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-3e9063503721462f8c32a7739ed2034f
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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