Pyridine → HCID 56837582, compound

HRID 410113Notes

Reaction equation

HRID 410113 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.[NH2:44][C:45]1[CH:46]=[C:47]([CH:50]=[CH:51][CH:52]=1)[C:48]#[N:49].N1C=CC=CC=1>C(#N)C>[C:48]([C:47]1[CH:46]=[C:45]([NH:44][C:36]([C:34]2[C:33]([O:39][CH2:40][CH:41]([F:42])[F:43])=[CH:32][C:29]3[N:30]([CH3:31])[C:26]([NH:25][C:11]4[C:12]([Cl:24])=[CH:13][CH:14]=[C:15]([CH2:16][NH:17][C:18](=[O:23])[C:19]([CH3:21])([CH3:22])[CH3:20])[C:10]=4[Cl:9])=[N:27][C:28]=3[CH:35]=2)=[O:38])[CH:52]=[CH:51][CH:50]=1)#[N:49]

Participants

6

Reactant 4

HCID 1049PyridineHCID 167023-AminobenzonitrileHCID 6407921-Chloro-N,N-2-trimethylpropenylamine2×HCID 86669634HCID 86669634, compound

Product 1

HCID 56837582HCID 56837582, 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 2.0 mL acetonitrile and it is stirred 10 min at rt. Additional (1-chloro-2-methyl-propenyl)-dimethylamine (20 μl) is added and the mixture is stirred for additional 20 min at rt. The crude acid chloride solution is added to a mixture of 3-aminobenzonitrile (12 mg, 0.10 mmol), pyridine (24 μL, 0.30 mmol) and acetonitrile (1.0 mL) and it is stirred for 15 min at rt and additional 5 h at 55° C. The solvent is removed in vacuo and the residue is dissolved in 2 mL of a 19:1 DMF/water-solution and is purified via preparative HPLC to furnish the title compound.

Workup

  1. stirringthe mixture is stirred for additional 20 min at rt
  2. stirringis stirred for 15 min at rt and additional 5 h at 55° C
  3. customThe solvent is removed in vacuo
  4. dissolutionthe residue is dissolved in 2 mL of a 19:1 DMF/water-solution
  5. customis purified via preparative HPLC

Sources & evidence

ORD record
ord-a92f724334d54cd6ab324b6bf86f77a5
Source dataset
uspto-grants-2014_06
Patent number
US08759537B2

Reaction notes

Loading…