1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59200055, compound

HRID 2381960Notes

Reaction equation

HRID 2381960 reaction equation
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]([OH:15])=O)=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.CCN(C(C)C)C(C)C.[CH3:46][N:47]([C:49]1[CH:54]=[CH:53][C:52]([C:55]([F:58])([F:57])[F:56])=[CH:51][N:50]=1)[NH2:48]>C(Cl)Cl>[CH3:46][N:47]([C:49]1[CH:54]=[CH:53][C:52]([C:55]([F:58])([F:56])[F:57])=[CH:51][N:50]=1)[NH:48][C:13]([C:10]1[CH:11]=[N:12][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][CH:9]=1)=[O:15]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 7473892-Phenylpyrimidine-5-carboxylic acidHCID 27777822-(1-Methylhydrazinyl)-5-(trifluoromethyl)pyridine

Product 1

HCID 59200055HCID 59200055, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-phenyl-pyrimidine-5-carboxylic acid (100 mg, 0.52 mmol), 1-hydroxybenzotriazole (77 mg, 0.57 mmol), 1-[3-(dimethylamino)propyl-3-ethylcarbodiimide (111 mg, 0.57 mmol) and DIPEA (0.57 mmol) in DCM (5 mL) is added N-methyl-N-(5-trifluoromethyl-pyridin-2-yl)-hydrazine (109 mg, 0.57 mmol). The reaction mixture is stirred at rt for 18 hours and then concentrated. The residue is purified by silica gel chromatography eluting with 10-75% EtOAc in heptane to afford 2-phenyl-pyrimidine-5-carboxylic acid N′-methyl-N′-[5-trifluoromethyl-pyridin-2-yl]-hydrazide as a solid (189 mg). MS: 374 (M+H); 1H NMR (300 MHz, CDCl3): δ 3.54 (s, 3H), 6.82 (d, 1H), 7.53-7.59 (m, 3H), 7.74 (d, 1H), 8.45 (d, 2H), 8.53 (d, 2H), 9.25 (s, 2H). IC50=100 nM.

Workup

  1. concentrationconcentrated
  2. customThe residue is purified by silica gel chromatography
  3. washeluting with 10-75% EtOAc in heptane

Sources & evidence

ORD record
ord-998120b25347453eac50da0025630129
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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