Phenylpropiolic Acid → N-(3-((thiazol-2-yl)amino)propyl)-3-phenylpropiolamide

HRID 1880644Notes

Reaction equation

HRID 1880644 reaction equation
C[N:2]([C:8]1[S:9][CH:10]=[CH:11][N:12]=1)[CH2:3][CH2:4][CH2:5][NH:6]C.[C:13]1([C:19]#[C:20][C:21]([OH:23])=O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C1COCC1>[S:9]1[CH:10]=[CH:11][N:12]=[C:8]1[NH:2][CH2:3][CH2:4][CH2:5][NH:6][C:21](=[O:23])[C:20]#[C:19][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 69475Phenylpropiolic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 69151207N1,N3-dimethyl-N1-(thiazol-2-yl)propane-1,3-diamine

Product 1

HCID 24887094N-(3-((thiazol-2-yl)amino)propyl)-3-phenylpropiolamideYield 42.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

440 mg (2.37 mmol) N1,N3-dimethyl-N1-(thiazol-2-yl)propane-1,3-diamine was dissolved, together with 347 mg (2.37 mmol) 3-phenyl propiolic acid, 412 μl (2.37 mmol) DIPEA and 761 mg (2.37 mmol) TBTU, in THF (30 ml), and stirred for 2 h at RT. The reaction solution was concentrated in vacuo and the residue was taken up by chloroform, washed with water and brine, dried over MgSO4 and concentrated in vacuo. CC (DCE/EtOH 10:1) was carried out on the residue, yielding 314 mg (1.00 mmol, 42%) N-(3-((thiazol-2-yl)amino)propyl)-3-phenylpropiolamide. MS [MH+] 314.1

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9f2a43c2431e49b69ad2b749eb3a0d71
Source dataset
uspto-grants-2012_11
Patent number
US08318774B2

Reaction notes

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