Ammonium Hydroxide → HCID 56932934, compound

HRID 1972613Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][N:18]=3)[C@@H:13]([CH2:33][N:34]([CH:39]([CH3:41])[CH3:40])[S:35]([CH3:38])(=[O:37])=[O:36])[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[NH4+:43]>CCO>[NH2:43][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][N:18]=3)[C@@H:13]([CH2:33][N:34]([CH:39]([CH3:41])[CH3:40])[S:35]([CH3:38])(=[O:37])=[O:36])[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A 5-mL microwave reaction vial charged with N-(((2R)-4-((6-chloro-3-pyridinyl)sulfonyl)-1-(5-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)-2-pyrimidinyl)-2-piperazinyl)methyl)-N-(1-methylethyl)methanesulfonamide (0.161 g, 0.246 mmol), concentrated ammonium hydroxide (0.65 mL, 5.0 mmol) and EtOH (2 mL). The vial was heated in an Initiator microwave reactor (Biotage AB, Inc., Uppsala, Sweden) at 140° C. for 2.5 h. The mixture was allowed to cool to room temperature and then concentrated in vacuo. The crude product was purified by column chromatography (25 g of silica gel, 30 to 100% EtOAc in hexanes) to afford N-(((2R)-4-((6-amino-3-pyridinyl)sulfonyl)-1-(5-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)-2-pyrimidinyl)-2-piperazinyl)methyl)-N-(1-methylethyl)methanesulfonamide (0.0873 g) as a white solid.

Workup

customA 5-mL microwave reaction
temperatureto cool to room temperature
concentrationconcentrated in vacuo
customThe crude product was purified by column chromatography (25 g of silica gel, 30 to 100% EtOAc in hexanes)

Sources & evidence

ORD record: ord-8178801775d04201a87ff09ea02506d4
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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