Water → HCID 67147704, compound

HRID 490541Notes

Reaction equation

HRID 490541 reaction equation
C(N(CC)CC)C.[F:8][C:9]([F:22])([F:21])[O:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.[CH3:23][O:24][C:25]1[CH:66]=[C:65]([O:67][CH3:68])[CH:64]=[CH:63][C:26]=1[CH2:27][NH:28][CH2:29][C:30]1[CH:35]=[CH:34][N:33]=[C:32]2[N:36]([S:53]([C:56]3[CH:61]=[CH:60][C:59]([CH3:62])=[CH:58][CH:57]=3)(=[O:55])=[O:54])[C:37]([C:39]3[C:47]4[C:42](=[CH:43][C:44]([O:50][CH3:51])=[C:45]([O:48][CH3:49])[CH:46]=4)[N:41]([CH3:52])[CH:40]=3)=[CH:38][C:31]=12.O>ClCCl>[CH3:23][O:24][C:25]1[CH:66]=[C:65]([O:67][CH3:68])[CH:64]=[CH:63][C:26]=1[CH2:27][N:28]([CH2:29][C:30]1[CH:35]=[CH:34][N:33]=[C:32]2[N:36]([S:53]([C:56]3[CH:57]=[CH:58][C:59]([CH3:62])=[CH:60][CH:61]=3)(=[O:55])=[O:54])[C:37]([C:39]3[C:47]4[C:42](=[CH:43][C:44]([O:50][CH3:51])=[C:45]([O:48][CH3:49])[CH:46]=4)[N:41]([CH3:52])[CH:40]=3)=[CH:38][C:31]=12)[S:17]([C:14]1[CH:15]=[CH:16][C:11]([O:10][C:9]([F:22])([F:21])[F:8])=[CH:12][CH:13]=1)(=[O:19])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 523102p-(Trifluoromethoxy)benzenesulphonyl chlorideHCID 67147711(2,4-dimethoxybenzyl) [2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]amine

Product 1

HCID 67147704HCID 67147704, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.052 cm3 of triethylamine and 0.265 cm3 of 4-(trifluoromethoxy)benzenesulfonyl chloride are added to a solution of 0.200 g of (2,4-dimethoxybenzyl)[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]amine in 6 cm3 of dichloromethane, under an argon atmosphere, at a temperature in the region of 20° C. The reaction medium is stirred at this same temperature for 24 hours. 2 cm3 of water are added. After separation of the phases by settling, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. After purification by flash-pack chromatography (SiO2, dichloromethane/methanol 98/02 by volume as eluent), 0.210 g of N-(2,4-dim ethoxybenzyl)-N-[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]-4-trifluoromethoxybenzenesulfonamide is obtained, the characteristics of which are as follows:

Workup

  1. customAfter separation of the phases
  2. dry with materialthe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customAfter purification by flash-pack chromatography (SiO2, dichloromethane/methanol 98/02 by volume as eluent)

Sources & evidence

ORD record
ord-78a1786fa48e4c32a05cb4ce7ef93f9f
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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