Pyridine → HCID 56839116, compound

HRID 410114Notes

Reaction equation

HRID 410114 reaction equation
ClC(N(C)C)=C(C)C.[Cl:9][C:10]1[C:15]([CH2:16][NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:14][CH:13]=[C:12]([Cl:24])[C:11]=1[NH:25][C:26]1[N:30]([CH3:31])[C:29]2[CH:32]=[C:33]([O:39][CH2:40][CH:41]([F:43])[F:42])[C:34]([C:36]([OH:38])=O)=[CH:35][C:28]=2[N:27]=1.[Cl:44][C:45]1[CH:51]=[C:50]([Cl:52])[CH:49]=[CH:48][C:46]=1[NH2:47].N1C=CC=CC=1>C(#N)C>[Cl:44][C:45]1[CH:51]=[C:50]([Cl:52])[CH:49]=[CH:48][C:46]=1[NH:47][C:36]([C:34]1[C:33]([O:39][CH2:40][CH:41]([F:42])[F:43])=[CH:32][C:29]2[N:30]([CH3:31])[C:26]([NH:25][C:11]3[C:12]([Cl:24])=[CH:13][CH:14]=[C:15]([CH2:16][NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:20])[CH3:21])[C:10]=3[Cl:9])=[N:27][C:28]=2[CH:35]=1)=[O:38]

Participants

6

Reactant 4

HCID 1049PyridineHCID 111232,4-DichloroanilineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 86669634HCID 86669634, compound

Product 1

HCID 56839116HCID 56839116, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

(1-Chloro-2-methyl-propenyl)-dimethylamine (20 μl) is added to a mixture of 2-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-(2,2-difluoro-ethoxy)-1-methyl-1H-benzimidazole-5-carboxylic acid (53 mg, 0.10 mmol) in 1.0 mL acetonitrile and it is stirred 15 min at rt. The crude acid chloride solution is added to a mixture of 2,4-dichloroaniline (16 mg, 0.10 mmol), pyridine (24 μL, 0.30 mmol) and acetonitrile (1.0 mL) and it is stirred over the weekend at 60° C. The solvent is removed in vacuo and the residue is dissolved in 2 mL of a 9:1 DMF/water-solution and is purified via preparative HPLC.

Workup

  1. stirringis stirred over the weekend at 60° C
  2. customThe solvent is removed in vacuo
  3. dissolutionthe residue is dissolved in 2 mL of a 9:1 DMF/water-solution
  4. customis purified via preparative HPLC

Sources & evidence

ORD record
ord-4b7ca5c4e2a446e7b9ba0921ce9c5c98
Source dataset
uspto-grants-2014_06
Patent number
US08759537B2

Reaction notes

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