Pyridine → HCID 46190289, compound

HRID 2360531Notes

Reaction equation

HRID 2360531 reaction equation
Cl.Cl.Cl.[NH2:4][C:5]1[C:6]([O:43][CH3:44])=[C:7]([NH:15][C:16]([C:18]2[N:19]([CH3:42])[C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][C:21]=3[CH2:27][N:28]2[CH2:33][CH2:32][N:31]([C:34]([CH:36]3[CH2:40][CH2:39][CH2:38][N:37]3[CH3:41])=[O:35])[CH2:30][CH2:29]2)=[O:17])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1.C(N(CC)CC)C.[CH2:52]([S:55](Cl)(=[O:57])=[O:56])[CH2:53][CH3:54].N1C=CC=CC=1>ClCCl>[C:11]([C:9]1[CH:10]=[C:5]([NH:4][S:55]([CH2:52][CH2:53][CH3:54])(=[O:57])=[O:56])[C:6]([O:43][CH3:44])=[C:7]([NH:15][C:16]([C:18]2[N:19]([CH3:42])[C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][C:21]=3[CH2:27][N:28]2[CH2:29][CH2:30][N:31]([C:34]([C@@H:36]3[CH2:40][CH2:39][CH2:38][N:37]3[CH3:41])=[O:35])[CH2:32][CH2:33]2)=[O:17])[CH:8]=1)([CH3:12])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 662791-Propanesulfonyl chloride2×HCID 66986130HCID 66986130, compound

Product 1

HCID 46190289HCID 46190289, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

200 mg of 1-methyl-7-[4-(1-methyl-pyrrolidine-2-carbonyl)-piperazin-1-ylmethyl]-1H-indole-2-carboxylic acid-(3-amino-5-tert-butyl-2-methoxy-phenyl)-amide trihydrochloride are dissolved in 2 ml dichloromethane and mixed successively with 210 μl triethylamine, 80 μl propylsulphonic acid chloride and 70 μl pyridine. The mixture is stirred for 2 hours at ambient temperature, a further 80 μl of propylsulphonic acid chloride are added and the mixture is stirred for a further 12 hours. The solvents are eliminated in vacuo and the residue is purified by preparative HPLC (method 3).

Workup

  1. stirringthe mixture is stirred for a further 12 hours
  2. customthe residue is purified by preparative HPLC (method 3)

Sources & evidence

ORD record
ord-04404d7dac6144bf86653359048593e3
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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