N-{3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-[(2-phenylpyrrolidin-1-yl)carbonyl]phenyl}-N-propylmethanesulfonamide → 3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-N-(1-methylbut-2-yn-1-yl)-5-[(methylsulfonyl)(propyl)amino]benzamide
Reaction equation
C(OC(NC(C)(CC1C=CC=CC=1)COCC1C=C(C=C(N(S(C)(=O)=O)CCC)C=1)C(O)=O)=O)(C)(C)C.CC(N)C#CC.[NH2:44][C:45]([CH3:83])([CH2:76][C:77]1[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=1)[CH2:46][O:47][CH2:48][C:49]1[CH:50]=[C:51]([N:68]([CH2:73][CH2:74][CH3:75])[S:69]([CH3:72])(=[O:71])=[O:70])[CH:52]=[C:53]([C:55]([N:57]2[CH2:61][CH2:60][CH2:59][CH:58]2[C:62]2C=CC=CC=2)=[O:56])[CH:54]=1>>[NH2:44][C:45]([CH3:83])([CH2:76][C:77]1[CH:78]=[CH:79][CH:80]=[CH:81][CH:82]=1)[CH2:46][O:47][CH2:48][C:49]1[CH:54]=[C:53]([CH:52]=[C:51]([N:68]([S:69]([CH3:72])(=[O:71])=[O:70])[CH2:73][CH2:74][CH3:75])[CH:50]=1)[C:55]([NH:57][CH:58]([CH3:62])[C:59]#[C:60][CH3:61])=[O:56]Participants
4
Reactant 3
Product 1
Procedure
3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-N-(1-methylbut-2-yn-1-yl)-5-[(methylsulfonyl)(propyl)amino]benzamide was prepared from 3-({2-[(tert-butoxycarbonyl)amino]-2-methyl-3-phenylpropoxy}methyl)-5-[(methylsulfonyl)(propyl)amino]benzoic acid (intermediate XI) and (1-methylbut-2-yn-1-yl)amine (intermediate XIII) following a similar procedure as described for the preparation of N-{3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-[(2-phenylpyrrolidin-1-yl)carbonyl]phenyl}-N-propylmethanesulfonamide. HRMS (ES, M+H) calculated for C27H37N3O4S: 500.2578, found: 500.2595.
Sources & evidence
- ORD record
- ord-167f7e06dccd411fa15437de6c2ac7cf
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07354942B2
Reaction notes
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