(Pyrimidin-5-yl)boronic acid → [4-((S)-2-Hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-[3-methyl-5-pyrimidin-5-yl-2-(3-trifluoromethoxy-phenyl)-3H-imidazol-4-yl]-methanone

HRID 545413Notes

Reaction equation

HRID 545413 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[N:17]([CH3:33])[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:32])([F:31])[F:30])[CH:23]=3)=[N:19][C:20]=2I)=[O:15])[CH2:10][CH2:9]1.[N:34]1[CH:39]=[C:38](B(O)O)[CH:37]=[N:36][CH:35]=1>>[OH:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[N:17]([CH3:33])[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:32])([F:31])[F:30])[CH:23]=3)=[N:19][C:20]=2[C:38]2[CH:39]=[N:34][CH:35]=[N:36][CH:37]=2)=[O:15])[CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 57541109[4-((S)-2-Hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-[5-iodo-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazol-4-yl]-methanone

Product 1

HCID 57541143[4-((S)-2-Hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-[3-methyl-5-pyrimidin-5-yl-2-(3-trifluoromethoxy-phenyl)-3H-imidazol-4-yl]-methanone

Procedure

In analogy to the procedure described for example 7, [4-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-[5-iodo-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-yl]-methanone (example 53) was reacted with pyrimidine-5-yl-boronic acid to give the title compound light brown oil. MS: 531.1 (MH+).

Sources & evidence

ORD record
ord-10f7ed5810c246ccae6dc409fcfb5269
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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