Acetohydrazide → N'-acetyl-3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)propanehydrazide

HRID 911872Notes

Reaction equation

HRID 911872 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15][C:16]([OH:18])=O)[N:13]=2)=[N:6][CH:7]=1.C1C=CC2N(O)N=NC=2C=1.O.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.[C:57]([NH:60][NH2:61])(=[O:59])[CH3:58]>C(#N)C.C1COCC1>[C:57]([NH:60][NH:61][C:16](=[O:18])[CH2:15][CH2:14][C:12]1[N:13]=[C:9]([NH:8][C:5]2[C:4]([O:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[S:10][CH:11]=1)(=[O:59])[CH3:58]

Participants

8

Reactant 5

HCID 14039AcetohydrazideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 577426713-(2-(5-Bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)propanoic acid

Product 1

HCID 86631510N'-acetyl-3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)propanehydrazideYield 127%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture 3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)propanoic acid (0.300 g, 0.714 mmol), HOBT-H2O (0.164 g, 1.07 mmol), DIEA (0.261 mL, 1.50 mmol), EDCI (0.205 g, 1.07 nmol), and acetohydrazide (0.106 g, 1.43 mmol) in 10 mL acetonitrile and 2 mL THF was stirred at 50° C. for 3 hours and then overnight at ambient temperature. The mixture was concentrated and diluted with CH2Cl2, washed with saturated aqueous NaHCO3, dried over Na2SO4, and concentrated to provide the title compound (0.431 g, 127% yield) that was carried directly on to the next step.

Workup

  1. customovernight
  2. customat ambient temperature
  3. concentrationThe mixture was concentrated
  4. additiondiluted with CH2Cl2
  5. washwashed with saturated aqueous NaHCO3
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-478db01288d34802b7baeb609fef06b6
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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