Dimethylamine → (1R*,2R*,5S*,6R*)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-{2-[(N,N-dimethylcarbamoyl)methyl]-2H-tetrazol-5-yl}-1-phenyl-8-azabicyclo[3.2.1]octane

HRID 2088210Notes

Reaction equation

HRID 2088210 reaction equation
[CH2:1]([N:8]1[C@@H]2[C@H](C(N)=O)C[C@@:9]1(C1C=CC=CC=1)[C@H](OCC1C=C(C(F)(F)F)C=C(C(F)(F)F)C=1)CC2)C1C=CC=CC=1.CNC.[CH2:44]([N:51]1[C@@H:56]2[C@H:57]([C:59]3[N:60]=[N:61][N:62]([CH2:64][C:65]([OH:67])=O)[N:63]=3)[CH2:58][C@@:52]1([C:84]1[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=1)[C@H:53]([O:68][CH2:69][C:70]1[CH:75]=[C:74]([C:76]([F:79])([F:78])[F:77])[CH:73]=[C:72]([C:80]([F:83])([F:82])[F:81])[CH:71]=1)[CH2:54][CH2:55]2)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>>[CH2:44]([N:51]1[C@@H:56]2[C@H:57]([C:59]3[N:60]=[N:61][N:62]([CH2:64][C:65](=[O:67])[N:8]([CH3:9])[CH3:1])[N:63]=3)[CH2:58][C@@:52]1([C:84]1[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=1)[C@H:53]([O:68][CH2:69][C:70]1[CH:75]=[C:74]([C:76]([F:79])([F:77])[F:78])[CH:73]=[C:72]([C:80]([F:83])([F:82])[F:81])[CH:71]=1)[CH2:54][CH2:55]2)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

4

Reactant 3

HCID 674DimethylamineHCID 86586702(1R*,2R*,5S*,6R*)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octan-6-carboxamideHCID 86586757(1R*,2R*,5S*,6R*)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(2-carboxymethyl-2H-tetrazol-5-yl)-1-phenyl-8-azabicyclo[3.2.1]octane

Product 1

HCID 86586759(1R*,2R*,5S*,6R*)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-{2-[(N,N-dimethylcarbamoyl)methyl]-2H-tetrazol-5-yl}-1-phenyl-8-azabicyclo[3.2.1]octane

Procedure

Prepared in analogous manner to (1R*,2R*,5S*,6R*)-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octan-6-carboxamide (Example 75) using dimethylamine (2.0M solution in THF) and (1R*,2R*,5S*,6R*)-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(2-carboxymethyl-2H-tetrazol-5-yl)-1-phenyl-8-azabicyclo[3.2.1]octane (Example 145).

Sources & evidence

ORD record
ord-57b311e503e94142818fb46aba1b1ce3
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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