Isopropylamine → 1-Oxo-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decane-8-sulfonic acid isopropylamide
Reaction equation
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9]([S:12](Cl)(=[O:14])=[O:13])[CH2:8][CH2:7]2)[CH2:5][CH2:4][N:3]1[C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=1.CCN(CC)CC.[CH:34]([NH2:37])([CH3:36])[CH3:35]>C(Cl)Cl>[CH:34]([NH:37][S:12]([N:9]1[CH2:10][CH2:11][C:6]2([C:2](=[O:1])[N:3]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[CH2:4][CH2:5]2)[CH2:7][CH2:8]1)(=[O:14])=[O:13])([CH3:36])[CH3:35]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A mixture of 74 mg (0.18 mmol) 1-Oxo-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decane-8-sulfonyl chloride, 73 mg (0.72 mmol) NEt3 and 14.8 mg (0.252 mmol) isopropylamine in 2 mL CH2Cl2 was stirred for 16 h at 50° C. The mixture was evaporated to dryness and the residue was subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid. The product containing fractions were evaporated to yield 12.5 mg (16%) of the title compound. MS (ESI): 436.4 (MH+).
Workup
- customThe mixture was evaporated to dryness
- customthe residue was subjected to purification by preparative HPLC on reversed phase
- washeluting with a gradient
- customformed from acetonitrile, water and formic acid
- additionThe product containing fractions
- customwere evaporated
Sources & evidence
- ORD record
- ord-8e60f4b570764d2e88f8089e690d8417
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329904B2
Reaction notes
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