Diisopropylethylamine → N-{[(2S)-4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}-N'-[3-(pyrrolidin-1-ylsulfonyl)propyl]urea
Reaction equation
[N:1]1([S:6]([CH2:9][CH2:10][CH2:11][NH2:12])(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[Cl:22][C:23]1[CH:24]=[C:25]([CH:47]=[CH:48][C:49]=1[Cl:50])[CH2:26][N:27]1[CH2:32][CH2:31][O:30][C@@H:29]([CH2:33][NH:34][C:35](=O)[O:36]C2C=CC([N+]([O-])=O)=CC=2)[CH2:28]1>CN(C)C=O.ClCCl>[Cl:22][C:23]1[CH:24]=[C:25]([CH:47]=[CH:48][C:49]=1[Cl:50])[CH2:26][N:27]1[CH2:32][CH2:31][O:30][C@@H:29]([CH2:33][NH:34][C:35]([NH:12][CH2:11][CH2:10][CH2:9][S:6]([N:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)(=[O:7])=[O:8])=[O:36])[CH2:28]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of Intermediate 28 (0.027 g) in N,N-dimethylformamide (1 ml) and dichloromethane (2 ml) containing N,N-diisopropylethylamine (0.041 ml) was added to a stirred solution of Intermediate 13 (0.051 g) in dry dichloromethane (2 ml) at room temperature under nitrogen, and the mixture was stirred at room temperature for 21 h. The mixture was applied directly to a sulphonic acid ion exchange cartridge (2 g Isolute SCX) and eluted with methanol (6 column volumes) followed by 10% 880 ammonia in methanol (3 column volumes); evaporation of the methanol/ammonia fractions gave the crude product (0.063 g). Purification by chromatography on silica gel (2 g Varian Bond Elut cartridge), eluting with chloroform, ether, ethyl acetate, acetone, and methanol, gave the title compound as a gum (0.036 g).
Workup
- washeluted with methanol (6 column volumes)
- customevaporation of the methanol/ammonia fractions
- customgave the crude product (0.063 g)
- customPurification by chromatography on silica gel (2 g Varian Bond Elut cartridge)
- washeluting with chloroform, ether, ethyl acetate, acetone, and methanol
Sources & evidence
- ORD record
- ord-268a5bc8954942f9b4c0a1cd60369d0d
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07157457B2
Reaction notes
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