Pyridine → HCID 136162347, compound

HRID 925478Notes

Reaction equation

HRID 925478 reaction equation
[CH3:1][N:2]([CH3:31])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[N:9][C:10]([C:13]2[CH:14]=[C:15]([CH:28]=[CH:29][CH:30]=2)[CH2:16][N:17]2[C:22](=[O:23])[CH:21]=[CH:20][C:19]([C:24]([NH:26][OH:27])=[NH:25])=[N:18]2)=[N:11][CH:12]=1.N1C=CC=CC=1.Cl[C:39](OCC)=[O:40]>CN(C=O)C>[CH3:31][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[N:9][C:10]([C:13]2[CH:14]=[C:15]([CH:28]=[CH:29][CH:30]=2)[CH2:16][N:17]2[C:22](=[O:23])[CH:21]=[CH:20][C:19]([C:24]3[NH:25][C:39](=[O:40])[O:27][N:26]=3)=[N:18]2)=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 178483580HCID 178483580, compound

Product 1

HCID 136162347HCID 136162347, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

500 mg (1.18 mmol) of 1-{3-[5-(3-dimethylaminopropoxy)pyrimidin-2-yl]-benzyl}-N-hydroxy-6-oxo-1,6-dihydropyridazine-3-carboxamidine are dissolved in 15 ml of DMF, and 286 μl (3.54 mmol) of pyridine are added. 124 μl (1.30 mmol) of ethyl chloroformate are subsequently added with stirring, and the solution is stirred at 80° C. for 15 and subsequently at 100° C. for 72 h. The reaction mixture is evaporated, and the residue is purified by means of preparative HPLC; yield: 21.2 mg of “A227” trifluoroacetate; HPLC: Rt=2.07 min; LC-MS: 450 (M+H).

Workup

  1. stirringthe solution is stirred at 80° C. for 15 and subsequently at 100° C. for 72 h
  2. customThe reaction mixture is evaporated
  3. customthe residue is purified by means of preparative HPLC

Sources & evidence

ORD record
ord-60f0b3d03cdf4b7781fed433bf912c53
Source dataset
uspto-grants-2016_03
Patent number
US09284300B2

Reaction notes

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