((R)-1-Piperidin-4-yl-pyrrolidin-2-yl)-methanol di-hydrochloride → [4-((S)-2-Hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-[5-iodo-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazol-4-yl]-methanone

HRID 545411Notes

Reaction equation

HRID 545411 reaction equation
[I:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]([F:17])([F:16])[F:15])[CH:8]=2)[N:4]([CH3:18])[C:3]=1[C:19]([OH:21])=O.Cl.Cl.[NH:24]1[CH2:29][CH2:28][CH:27]([N:30]2[CH2:34][CH2:33][CH2:32][C@@H:31]2[CH2:35][OH:36])[CH2:26][CH2:25]1>>[OH:36][CH2:35][C@@H:31]1[CH2:32][CH2:33][CH2:34][N:30]1[CH:27]1[CH2:28][CH2:29][N:24]([C:19]([C:3]2[N:4]([CH3:18])[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]([F:15])([F:17])[F:16])[CH:8]=3)=[N:6][C:2]=2[I:1])=[O:21])[CH2:25][CH2:26]1

Participants

3

Reactant 2

HCID 67133026((R)-1-Piperidin-4-yl-pyrrolidin-2-yl)-methanol di-hydrochloride2×HCID 671332555-iodo-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid

Product 1

HCID 57541109[4-((S)-2-Hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-[5-iodo-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazol-4-yl]-methanone

Procedure

In analogy to the procedure described for example 2, 5-iodo-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid (example 19) and ((S)-1-piperidin-4-yl-pyrrolidin-2-yl)-methanol di-hydrochloride [prepared as described for ((R)-1-piperidin-4-yl-pyrrolidin-2-yl)-methanol di-hydrochloride (intermediate 2), but starting from (S)-(−)-pyrrolidin-2-yl-methanol] gave the title compound as brown amorphous solid. MS: 579.1 (MH+).

Sources & evidence

ORD record
ord-32df5bcc465641978f048e4b7d097113
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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