Triethylamine → 4-Chloro-5-methanesulfonyloxy-7-{1-(tert-butoxycarbonyl)-5-[4-(2-hydroxyethyl)pyperazin-1-ylmethyl]indol-2-yl}isoindolinone

HRID 21266Notes

Reaction equation

HRID 21266 reaction equation
[Cl:1][C:2]1[C:10]([OH:11])=[CH:9][C:8]([C:12]2[N:13]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([CH2:21][N:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][OH:30])[CH2:24][CH2:23]2)=[CH:16][CH:15]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:38].C(N(CC)CC)C.[CH3:46][S:47](Cl)(=[O:49])=[O:48]>ClCCl>[Cl:1][C:2]1[C:10]([O:11][S:47]([CH3:46])(=[O:49])=[O:48])=[CH:9][C:8]([C:12]2[N:13]([C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])[C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([CH2:21][N:22]2[CH2:23][CH2:24][N:25]([CH2:28][CH2:29][OH:30])[CH2:26][CH2:27]2)=[CH:16][CH:15]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68532125HCID 68532125, compound

Product 1

HCID 874849664-Chloro-5-methanesulfonyloxy-7-{1-(tert-butoxycarbonyl)-5-[4-(2-hydroxyethyl)pyperazin-1-ylmethyl]indol-2-yl}isoindolinoneYield 425.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Step 1 of Example 289, 4-chloro-5-hydroxy-7-{1-(tert-butoxycarbonyl)-5-[4-(2-hydroxyethyl)pyperazin-1-ylmethyl]indol-2-yl}isoindolinone (62.5 mg, 0.0950 mmol) was dissolved in dichloromethane (2.4 mL), and the solution was treated with triethylamine (0.053 mL, 0.38 mmol) and methanesulfonyl chloride (0.015 mL, 0.019 mmol), followed by purification by slurry using hexane to obtain 4-chloro-5-methanesulfonyloxy-7-{1-(tert-butoxycarbonyl)-5-[4-(2-hydroxyethyl)pyperazin-1-ylmethyl]indol-2-yl}isoindolinone (50.1 mg, yield 72%).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-04a6c367970b45f48c9c6b10266b820f
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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