4-(1-Pyrrolidinyl)piperidine → HCID 25190072, compound

HRID 1692436Notes

Reaction equation

HRID 1692436 reaction equation
[CH3:1][C:2]1[C:3]([C:24](O)=[O:25])=[C:4]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[CH:7]=1.[N:27]1([CH:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH2:31][CH2:30][CH2:29][CH2:28]1>>[CH3:1][C:2]1[C:3]([C:24]([N:35]2[CH2:36][CH2:37][CH:32]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH2:33][CH2:34]2)=[O:25])=[C:4]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:15])([F:16])[F:17])[CH:9]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 787034-(1-Pyrrolidinyl)piperidineHCID 66901655HCID 66901655, compound

Product 1

HCID 25190072HCID 25190072, compound

Procedure

In analogy to the procedures described in example 1, intermediate 11 E and in example 47, the title compound has been prepared by the following reaction sequence: i) 5-methyl-3-trifluoromethanesulfonyloxy-3′-trifluoromethyl-biphenyl-4-carboxylic acid methyl ester (intermediate 11 C) was reacted with pyridine-3-yl-boronic acid in DMF at 80° C. in the presence of potassium phosphate solution and tetrakis-(triphenylphosphine)-palladium to give 5-methyl-3-pyridin-3-yl-3′-trifluoromethyl-biphenyl-4-carboxylic acid methyl ester; ii) saponification of 5-methyl-3-pyridin-3-yl-3′-trifluoromethyl-biphenyl-4-carboxylic acid methyl ester gave 5-methyl-3-pyridin-3-yl-3′-trifluoromethyl-biphenyl-4-carboxylic acid; iii) transformation of 5-methyl-3-pyridin-3-yl-3′-trifluoromethyl-biphenyl-4-carboxylic acid into its acid chloride and reaction with 4-pyrrolidin-1-yl-piperidine gave the title compound as off-white amorphous solid. MS: 494.3 (MH+).

Sources & evidence

ORD record
ord-d7a2629e7e2d4345804ffad111b3f55e
Source dataset
uspto-grants-2012_04
Patent number
US08153805B2

Reaction notes

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