((S)-1-piperidin-4-yl-pyrrolidin-2-yl)-methanol dihydrochloride → [4-((s)-2-Hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-[5-methyl-3-pyrimidin-5-yl-1-(3-trifluoromethyl-phenyl)-1h-pyrazol-4-yl]-methanone

HRID 1011991ノート

反応式

HRID 1011991 の反応式
[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[N:5]=[C:4]([C:17]2[CH:18]=[N:19][CH:20]=[N:21][CH:22]=2)[C:3]=1[C:23](O)=[O:24].BrC1C=CC(N2C(C)=C(C(O)=O)C(C3C=NC=NC=3)=N2)=CC=1C(F)(F)F.Cl.Cl.[NH:54]1[CH2:59][CH2:58][CH:57]([N:60]2[CH2:64][CH2:63][CH2:62][C@H:61]2[CH2:65][OH:66])[CH2:56][CH2:55]1>>[OH:66][CH2:65][C@@H:61]1[CH2:62][CH2:63][CH2:64][N:60]1[CH:57]1[CH2:58][CH2:59][N:54]([C:23]([C:3]2[C:4]([C:17]3[CH:22]=[N:21][CH:20]=[N:19][CH:18]=3)=[N:5][N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:14])[F:15])[CH:8]=3)[C:2]=2[CH3:1])=[O:24])[CH2:55][CH2:56]1

参加物

4

反応物 3

HCID 66901571((S)-1-piperidin-4-yl-pyrrolidin-2-yl)-methanol dihydrochlorideHCID 673152105-methyl-3-pyrimidin-5-yl-1-(3-trifluoromethyl-phenyl)-1H-pyrazole-4-carboxylic acidHCID 673155081-(4-bromo-3-trifluoromethyl-phenyl)-5-methyl-3-pyrimidin-5-yl-1H-pyrazole-4-carboxylic acid

生成物 1

HCID 57555044[4-((s)-2-Hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-[5-methyl-3-pyrimidin-5-yl-1-(3-trifluoromethyl-phenyl)-1h-pyrazol-4-yl]-methanone

実験手順

In analogy to the procedure described in Example 160E], a mixture of 5-methyl-3-pyrimidin-5-yl-1-(3-trifluoromethyl-phenyl)-1H-pyrazole-4-carboxylic acid and 1-(4-bromo-3-trifluoromethyl-phenyl)-5-methyl-3-pyrimidin-5-yl-1H-pyrazole-4-carboxylic acid (example 173D]) and ((S)-1-piperidin-4-yl-pyrrolidin-2-yl)-methanoldihydrochloride (Example 161A]) gave a mixture of the title compound and example 176. Purification by reversed phase HPLC (MeCN:H2O) afforded [1-(4-bromo-3-trifluoromethyl-phenyl)-5-methyl-3-pyrimidin-5-yl-1H-pyrazol-4-yl]-[4-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-methanone (Example 176) and [4-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-[5-methyl-3-pyrimidin-5-yl-1-(3-trifluoromethyl-phenyl)-1H-pyrazol-4-yl]-methanone as a white solid (32%). MS: 515.5 (MH+).

後処理

  1. customgave

出典と根拠

ORDレコード
ord-fd79793bf78e494babd68688552e5207
出典データセット
uspto-grants-2011_07
特許番号
US07977358B2

反応ノート

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