Ammonium Hydroxide → HCID 56933050, compound

HRID 1972678Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH: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][CH:18]=2)[CH2:13][CH2:12]1)(=[O:10])=[O:9].[OH-].[NH4+:34]>C(O)C>[NH2:34][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH: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][CH:18]=2)[CH2:13][CH2:12]1)(=[O:10])=[O:9]

Participants

Conditions

Temperature: 110 °C

Procedure

To a 2-mL microwave vial was added 2-(4-(4-((4-chloro-3-pyridinyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (90 mg, 0.18 mmol), ethanol (1.5 mL) and aqueous ammonium hydroxide (1.5 mL, 39 mmol). The solution was then heated in the microwave at 110° C. for 2 h and then concentrated. The residue was diluted with saturated aqueous NaHCO3 and DCM. The solution was stirred for 5 min and then transferred onto a phase separation cartridge (Radleys Discovery Technologies) with the organic phase being collected and passed through a plug of Na2SO4. The collected solution was concentrated and purified by silica gel chromatography (0 to 5.0% MeOH/DCM) afforded 2-(4-(4-((4-amino-3-pyridinyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (63 mg) as a white solid.

Workup

concentrationconcentrated
additionThe residue was diluted with saturated aqueous NaHCO3 and DCM
customtransferred onto a phase separation cartridge (Radleys Discovery Technologies) with the organic phase
custombeing collected
concentrationThe collected solution was concentrated
custompurified by silica gel chromatography (0 to 5.0% MeOH/DCM)

Sources & evidence

ORD record: ord-2c5f253cf3cc44208028de140c1d23fb
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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