Methanesulfonyl chloride → N-Cyclopropyl-3-fluoro-5-[2-(3-hydroxy-2,2-dimethylpropyl)-4-{[(3S)-3-methylpiperazin-1-yl]methyl}-1-oxo-1,2-dihydroisoquinolin-6-yl]-4-methylbenzamide hydrochloride

HRID 906431Notes

Reaction equation

HRID 906431 reaction equation
[Si]([O:8][CH2:9][C:10]([CH3:40])([CH3:39])[CH2:11][N:12]1[CH:21]=[C:20]([CH2:22]O)[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:24]3[CH:25]=[C:26]([CH:33]=[C:34]([F:37])[C:35]=3[CH3:36])[C:27]([NH:29][CH:30]3[CH2:32][CH2:31]3)=[O:28])[CH:18]=2)[C:13]1=[O:38])(C(C)(C)C)(C)C.CS([Cl:45])(=O)=O.[CH3:46][C@H:47]1[CH2:52][NH:51][CH2:50][CH2:49][N:48]1C(OC(C)(C)C)=O>>[ClH:45].[CH:30]1([NH:29][C:27](=[O:28])[C:26]2[CH:25]=[C:24]([C:17]3[CH:18]=[C:19]4[C:14](=[CH:15][CH:16]=3)[C:13](=[O:38])[N:12]([CH2:11][C:10]([CH3:39])([CH3:40])[CH2:9][OH:8])[CH:21]=[C:20]4[CH2:22][N:51]3[CH2:50][CH2:49][NH:48][C@@H:47]([CH3:46])[CH2:52]3)[C:35]([CH3:36])=[C:34]([F:37])[CH:33]=2)[CH2:32][CH2:31]1

Participants

4

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 10081508tert-Butyl (2S)-2-methylpiperazine-1-carboxylateHCID 673911003-[2-(3-{[tert-Butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)-4-(hydroxymethyl)-1-oxo-1,2-dihydroisoquinolin-6-yl]-N-cyclopropyl-5-fluoro-4-methylbenzamide

Product 1

HCID 67136087N-Cyclopropyl-3-fluoro-5-[2-(3-hydroxy-2,2-dimethylpropyl)-4-{[(3S)-3-methylpiperazin-1-yl]methyl}-1-oxo-1,2-dihydroisoquinolin-6-yl]-4-methylbenzamide hydrochloride

Procedure

The subtitle product was made from 3-[2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)-4-(hydroxymethyl)-1-oxo-1,2-dihydroisoquinolin-6-yl]-N-cyclopropyl-5-fluoro-4-methylbenzamide (Example 26 g, 190 mg) by sequential reaction with methanesulfonyl chloride (57 μL) and tert-butyl (2S)-2-methylpiperazine-1-carboxylate (240 mg) using a similar method to Example 26 h, to afford the title compound (58 mg) as a white solid.

Workup

  1. customto Example 26 h

Sources & evidence

ORD record
ord-c706d40c85c042738312a62776fe5bb1
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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