Diisopropylamine → HCID 56932771, compound

HRID 1972570Notes

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

A 5-mL microwave vial was charged with ((2R)-4-(thiophen-2-ylsulfonyl)-1-(4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl)piperazin-2-yl)methyl methanesulfonate (0.200 g, 0.378 mmol, Intermediate B) diisopropylamine (0.077 g, 0.757 mmol), potassium carbonate (0.105 g, 0.757 mmol), in 3 mL of MeCN. The vial was sealed and heated in an Initiator microwave reactor (Biotage AB, Inc., Uppsala, Sweden) at 140° C. for 30 min. The reaction mixture was filtered and the filtrate was concentrated. The crude product was purified by column chromatography on silica gel (40 g of silica gel, 10 to 40% EtOAc in hexanes) to afford 2-(4-((2S)-2-((bis(1-methylethyl)amino)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol (0.130 g) as

Workup

customThe vial was sealed
filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated
customThe crude product was purified by column chromatography on silica gel (40 g of silica gel, 10 to 40% EtOAc in hexanes)

Sources & evidence

ORD record: ord-1aef3c760f8043bdb697cfb376948dd6
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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