Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Methanol | HCID 887 | — |
| Reactant | ((2R)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl methanesulfonate | HCID 86670301 | — |
| Product | Ammonia | HCID 222 | 2% |
| Product | 2-(4-((2S)-2-(aminomethyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol | HCID 66582560 | — |
Reaction Steps
To a 20 mL of microwave vial was added ((2R)-4-(thiophen-2-ylsulfonyl)-1-(4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl)piperazin-2-yl)methyl methanesulfonate (1.0 g, 1.9 mmol, Intermediate B) and ammonia, 2M solution in methanol (9.5 mL, 19 mmol, Aldrich, St. Louis, Mo.). 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 concentrated and the crude product was purified by column chromatography (80 g of silica gel, 100% CH2Cl2 first then 2 to 5% 2M NH3 in CH2Cl2) to afford 2-(4-((2S)-2-(aminomethyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol (0.540 g) as a white foam.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08431563B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-5e302612a4a84677bc1270cb0277ea75 |
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| Source note | uspto-grants-2013_04 |
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