3-(3-Chlorophenyl)-2-propynoic acid → 3-(3-chlorophenyl)-N-(2-(methyl(5-methylthiazol-2-yl)amino)ethyl)-propiolamide

HRID 252933Notes

Reaction equation

HRID 252933 reaction equation
N=C=N.[CH3:4][N:5]([C:9]1[S:10][C:11]([CH3:14])=[CH:12][N:13]=1)[CH2:6][CH2:7][NH2:8].[Cl:15][C:16]1[CH:17]=[C:18]([C:22]#[C:23][C:24](O)=[O:25])[CH:19]=[CH:20][CH:21]=1.CN(C1SC=CN=1)CCNC(=O)C#CC1C=CC=C(Cl)C=1>C(Cl)Cl>[Cl:15][C:16]1[CH:17]=[C:18]([C:22]#[C:23][C:24]([NH:8][CH2:7][CH2:6][N:5]([CH3:4])[C:9]2[S:10][C:11]([CH3:14])=[CH:12][N:13]=2)=[O:25])[CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 238793-(3-Chlorophenyl)-2-propynoic acidHCID 160435CarbodiimideHCID 16656753N-(2-(methyl(thiazol-2-yl)amino)ethyl)-3-(3-chlorophenyl)-propiolamideHCID 68418681N1-methyl-N1-(5-methylthiazol-2-yl)ethane-1,2-diamine

Product 1

HCID 577741793-(3-chlorophenyl)-N-(2-(methyl(5-methylthiazol-2-yl)amino)ethyl)-propiolamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.19 g (˜2.6 mmol) of PS carbodiimide were added to a solution of 232 mg (1.35 mmol) of N1-methyl-N1-(5-methylthiazol-2-yl)ethane-1,2-diamine and 367 mg (2.03 mmol) of (3-chlorophenyl)propiolic acid in DCM (40 ml). The mixture was then shaken for 16 h at RT, after which the resin was filtered out and rinsed with DCM and EtOH. The filtrate was evaporated under a vacuum and CC (DCE/EtOH 5:1) was carried out with the residue, 169 mg (0.51 mmol, 37%) of N-(2-(methyl(thiazol-2-yl)amino)ethyl)-3-(3-chlorophenyl)-propiolamide being obtained. MS [MH+] 334.1

Workup

  1. filtrationafter which the resin was filtered out
  2. washrinsed with DCM and EtOH
  3. customThe filtrate was evaporated under a vacuum and CC (DCE/EtOH 5:1)
  4. customobtained

Sources & evidence

ORD record
ord-0170e5a770154b6ebf1635bde16f92af
Source dataset
uspto-grants-2011_01
Patent number
US07871999B2

Reaction notes

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