Dipropylamine → 3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-[(methylsulfonyl)(propyl)amino]-N,N-dipropylbenzamide

HRID 899477Notes

Reaction equation

HRID 899477 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.C(NCCC)CC.[NH2:45][C:46]([CH3:84])([CH2:77][C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1)[CH2:47][O:48][CH2:49][C:50]1[CH:51]=[C:52]([N:69]([CH2:74][CH2:75][CH3:76])[S:70]([CH3:73])(=[O:72])=[O:71])[CH:53]=[C:54]([C:56]([N:58]2[CH2:62][CH2:61][CH2:60][CH:59]2[C:63]2C=CC=C[CH:64]=2)=[O:57])[CH:55]=1>>[NH2:45][C:46]([CH3:84])([CH2:77][C:78]1[CH:79]=[CH:80][CH:81]=[CH:82][CH:83]=1)[CH2:47][O:48][CH2:49][C:50]1[CH:55]=[C:54]([CH:53]=[C:52]([N:69]([S:70]([CH3:73])(=[O:72])=[O:71])[CH2:74][CH2:75][CH3:76])[CH:51]=1)[C:56]([N:58]([CH2:59][CH2:63][CH3:64])[CH2:62][CH2:61][CH3:60])=[O:57]

Participants

4

Reactant 3

HCID 8902DipropylamineHCID 11215160N-{3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-[(2-phenylpyrrolidin-1-yl)carbonyl]phenyl}-N-propylmethanesulfonamideHCID 588563373-({2-[(Tert-butoxycarbonyl)amino]-2-methyl-3-phenylpropoxy}methyl)-5-[(methylsulfonyl)(propyl)amino]benzoic acid2×

Product 1

HCID 588563533-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-[(methylsulfonyl)(propyl)amino]-N,N-dipropylbenzamide

Procedure

3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-[(methylsulfonyl)(propyl)amino]-N,N-dipropylbenzamide was prepared from 3-({2-[(tert-butoxycarbonyl)amino]-2-methyl-3-phenylpropoxy}methyl)-5-[(methylsulfonyl)(propyl)amino]benzoic acid (intermediate XI) and dipropylamine 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 C28H43N3O4S: 518.3047, found: 518.3051.

Sources & evidence

ORD record
ord-b41cfab0301d40848b686879e25307da
Source dataset
uspto-grants-2008_04
Patent number
US07354942B2

Reaction notes

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