(4-Bromo-2,6-dimethyl-phenyl)-[4-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-methanone → benzoic acid (S)-1-{1-[2-(3,5-bis-trifluoromethyl-phenyl)-4,6-dimethyl-pyrimidine-5-carbonyl]-piperidin-4-yl}-pyrrolidin-2-ylmethyl ester

HRID 1692408Notes

Reaction equation

HRID 1692408 reaction equation
BrC1C=C(C)C(C(N2CCC(N3CCCC3)CC2)=O)=C(C)C=1.BrC1C=C(C)C(C(N2CCC(N3CCC[C@H]3CO)CC2)=O)=C(C)C=1.[F:47][C:48]([F:81])([F:80])[C:49]1[CH:50]=[C:51]([C:59]2[N:64]=[C:63]([CH3:65])[C:62]([C:66]([N:68]3[CH2:73][CH2:72][CH:71]([N:74]4[CH2:78][CH2:77][CH2:76][CH2:75]4)[CH2:70][CH2:69]3)=[O:67])=[C:61]([CH3:79])[N:60]=2)[CH:52]=[C:53]([C:55]([F:58])([F:57])[F:56])[CH:54]=1.N1CCC(N2CCC[C@H]2[CH2:93][O:94][C:95](=[O:102])[C:96]2[CH:101]=[CH:100][CH:99]=[CH:98][CH:97]=2)CC1>>[F:58][C:55]([F:56])([F:57])[C:53]1[CH:52]=[C:51]([C:59]2[N:64]=[C:63]([CH3:65])[C:62]([C:66]([N:68]3[CH2:69][CH2:70][CH:71]([N:74]4[CH2:78][CH2:77][CH2:76][C@H:75]4[CH2:93][O:94][C:95](=[O:102])[C:96]4[CH:101]=[CH:100][CH:99]=[CH:98][CH:97]=4)[CH2:72][CH2:73]3)=[O:67])=[C:61]([CH3:79])[N:60]=2)[CH:50]=[C:49]([C:48]([F:47])([F:80])[F:81])[CH:54]=1

Participants

5

Reactant 4

HCID 44473778(4-Bromo-2,6-dimethyl-phenyl)-[4-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-methanoneHCID 57580536[2-(3,5-Bis-trifluoromethyl-phenyl)-4,6-dimethyl-pyrimidin-5-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanoneHCID 66901590benzoic acid (S)-1-piperidin-4-yl-pyrrolidin-2-ylmethyl ester2×HCID 66901599(4-Bromo-2,6-dimethyl-phenyl)-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

Product 1

HCID 86627850benzoic acid (S)-1-{1-[2-(3,5-bis-trifluoromethyl-phenyl)-4,6-dimethyl-pyrimidine-5-carbonyl]-piperidin-4-yl}-pyrrolidin-2-ylmethyl ester

Procedure

In analogy to the procedures described for intermediate 1 and for intermediate 4 B), 2-(3,5-bis-trifluoromethyl-phenyl)-4,6-dimethyl-pyrimidine-5-carboxylic acid (example 15) was converted into its acid chloride and subsequently reacted with benzoic acid (S)-1-piperidin-4-yl-pyrrolidin-2-ylmethyl ester (intermediate 3) to give benzoic acid (S)-1-{1-[2-(3,5-bis-trifluoromethyl-phenyl)-4,6-dimethyl-pyrimidine-5-carbonyl]-piperidin-4-yl}-pyrrolidin-2-ylmethyl ester, which was subsequently saponified to give the title compound as colorless solid. MS: 531.2 (MH+).

Sources & evidence

ORD record
ord-ae3f1b668c7845d99a0f83ecbc1dea84
Source dataset
uspto-grants-2012_04
Patent number
US08153805B2

Reaction notes

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