Ammonia → N-{3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-[(2-phenylpyrrolidin-1-yl)carbonyl]phenyl}-N-propylmethanesulfonamide

HRID 899475Notes

Reaction equation

HRID 899475 reaction equation
C(OC([NH:8][C:9]([CH3:37])([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:10][O:11][CH2:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([N:22]([S:26]([CH3:29])(=[O:28])=[O:27])[CH2:23][CH2:24][CH3:25])[CH:21]=1)[C:16](O)=[O:17])=O)(C)(C)C.[C:38]1([CH:44]2[CH2:48][CH2:47][CH2:46][NH:45]2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.NC(C)(CC1C=CC=CC=1)COCC1C=C(C=C(N(S(C)(=O)=O)CCC)C=1)C(NC(C1C=CC=CC=1)C(F)(F)F)=O.N>CO>[NH2:8][C:9]([CH3:37])([CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:10][O:11][CH2:12][C:13]1[CH:21]=[C:20]([N:22]([CH2:23][CH2:24][CH3:25])[S:26]([CH3:29])(=[O:28])=[O:27])[CH:19]=[C:15]([C:16]([N:45]2[CH2:46][CH2:47][CH2:48][CH:44]2[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:17])[CH:14]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 2618922-PhenylpyrrolidineHCID 114902383-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-[(methylsulfonyl)(propyl)amino]-N-(2,2,2-trifluoro-1-phenylethyl)benzamideHCID 588563373-({2-[(Tert-butoxycarbonyl)amino]-2-methyl-3-phenylpropoxy}methyl)-5-[(methylsulfonyl)(propyl)amino]benzoic acid2×

Product 1

HCID 11215160N-{3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-[(2-phenylpyrrolidin-1-yl)carbonyl]phenyl}-N-propylmethanesulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

N-{3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-[(2-phenylpyrrolidin-1-yl)carbonyl]phenyl}-N-propylmethanesulfonamide was prepared from 3-({2-[(tert-butoxycarbonyl)amino]-2-methyl-3-phenylpropoxy}methyl)-5-[(methylsulfonyl)(propyl)amino]benzoic acid (intermediate XI) and 2-phenylpyrrolidine following a similar procedure as described for the preparation of 3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-[(methylsulfonyl)(propyl)amino]-N-(2,2,2-trifluoro-1-phenylethyl)benzamide with additional purification by ion exchange chromatography (Varian Bond Elut SCX, eluting with MeOH followed by 2.0M.NH3 in MeOH). HRMS (ES, M+H) calculated for C32H41N3O4S: 564.2891, found: 564.2891.

Sources & evidence

ORD record
ord-69f4b1af1ba24bd0820944565f014999
Source dataset
uspto-grants-2008_04
Patent number
US07354942B2

Reaction notes

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