Triethylamine → HCID 46190291, compound

HRID 2360532Notes

Reaction equation

HRID 2360532 reaction equation
[NH2:1][C:2]1[C:3]([O:43][CH3:44])=[C:4]([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]([C@@H:36]3[CH2:40][CH2:39][CH2:38][N:37]3[CH3:41])=[O:35])[CH2:30][CH2:29]2)=[O:17])[CH:5]=[C:6]([C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10])[CH:7]=1.C(N(CC)CC)C.[CH3:52][S:53](Cl)(=[O:55])=[O:54].[OH-].[Na+]>ClCCl.CO>[CH3:52][S:53]([NH:1][C:2]1[C:3]([O:43][CH3:44])=[C:4]([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:5]=[C:6]([C:8]([F:13])([F:14])[C:9]([F:12])([F:10])[F:11])[CH:7]=1)(=[O:55])=[O:54]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chloride2×HCID 58493961HCID 58493961, compound

Product 1

HCID 46190291HCID 46190291, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

70 mg (S)-1-methyl-7-[4-(1-methyl-pyrrolidine-2-carbonyl)-piperazin-1-ylmethyl]-1H-indole-2-carboxylic acid-(3-amino-2-methoxy-5-pentafluoroethyl-phenyl)-amide are dissolved in 2 ml dichloromethane, combined with 36 μl triethylamine, and 20 μl methanesulphonic acid chloride are added dropwise to this mixture. It is stirred for 2 hours, a further 20 μl methanesulphonic acid chloride and 36 μl triethylamine are added and then it is stirred for 1.5 hours. Then 2 ml of methanol and 600 μl of 2 N sodium hydroxide solution are added. The mixture is stirred for 2 hours, the solvents are eliminated in vacuo and the residue is chromatographed on silica gel (dichloromethane/(methanol/ammonia in methanol (saturated) 9:1) 99:1 to 85:15).

Workup

  1. additionare added dropwise to this mixture
  2. stirringit is stirred for 1.5 hours
  3. stirringThe mixture is stirred for 2 hours
  4. customthe residue is chromatographed on silica gel (dichloromethane/(methanol/ammonia in methanol (saturated) 9:1) 99:1 to 85:15)

Sources & evidence

ORD record
ord-1c3812f18b174c3bb4165a3436ee2cce
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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