Water → 3-Methyl-4-{2-[2-(3-{2-[2-(2-methylamino-ethoxy)-ethoxy]-ethoxy}-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-benzoic acid hydrochloride

HRID 1755124Notes

Reaction equation

HRID 1755124 reaction equation
C(OC([N:8]1[C:12](=[O:13])[C:11]2([CH2:18][CH2:17][N:16]([S:19]([CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]([O:32]C(C)(C)C)=[O:31])=[CH:26][C:25]=3[CH3:37])(=[O:21])=[O:20])[CH2:15][CH2:14]2)[N:10]=[C:9]1[C:38]1[CH:43]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:41]=[C:40]([O:48][CH2:49][CH2:50][O:51][CH2:52][CH2:53][O:54][CH2:55][CH2:56][N:57](C(OC(C)(C)C)=O)[CH3:58])[CH:39]=1)=O)(C)(C)C.O.[ClH:67].O1CCOCC1>>[ClH:67].[CH3:37][C:25]1[CH:26]=[C:27]([CH:28]=[CH:29][C:24]=1[CH2:23][CH2:22][S:19]([N:16]1[CH2:15][CH2:14][C:11]2([N:10]=[C:9]([C:38]3[CH:43]=[C:42]([C:44]([F:45])([F:46])[F:47])[CH:41]=[C:40]([O:48][CH2:49][CH2:50][O:51][CH2:52][CH2:53][O:54][CH2:55][CH2:56][NH:57][CH3:58])[CH:39]=3)[NH:8][C:12]2=[O:13])[CH2:18][CH2:17]1)(=[O:20])=[O:21])[C:30]([OH:32])=[O:31]

Participants

4

Reactant 3

HCID 962WaterHCID 204431481,4-Dioxane hydrochlorideHCID 86672799HCID 86672799, compound

Product 1

HCID 668171943-Methyl-4-{2-[2-(3-{2-[2-(2-methylamino-ethoxy)-ethoxy]-ethoxy}-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-benzoic acid hydrochlorideYield 98%

Procedure

2-[3-(2-{2-[2-(tert-Butoxycarbonyl-methyl-amino)-ethoxy]-ethoxy}-ethoxy)-5-trifluoromethyl-phenyl]-8-[2-(4-tert-butoxycarbonyl-2-methyl-phenyl)-ethanesulfonyl]-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-3-carboxylic acid tert-butyl ester (37.4 mg, 39.7 μmol) was dissolved in 4 N hydrochloric acid-dioxane (0.79 mL). Water (14.3 μL, 795 μmol) was added and the mixture was stirred at room temperature for three hours. The reaction solution was concentrated under reduced pressure to give 3-methyl-4-{2-[2-(3-{2-[2-(2-methylamino-ethoxy)-ethoxy]-ethoxy}-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-benzoic acid hydrochloride (28.0 mg, 98%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4cc3c4e0e25e4574bd2b7f14728a34c8
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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