4-{4-[6-Chloro-2-oxo-5-(trifluoromethyl)-2,3-dihydro-1H-benzimidazol-1-yl]-1-piperidinyl}tetrahydro-2H-pyran-4-carbonitrile → 6-Chloro-1-[1-(4-methyltetrahydro-2H-pyran-4-yl)-4-piperidinyl]-5-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-one hydrochloride

HRID 2064216ノート

反応式

HRID 2064216 の反応式
[Cl:1][C:2]1[C:3]([C:26]([F:29])([F:28])[F:27])=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]4([C:23]#N)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[CH2:13][CH2:12]3)[C:6]=2[CH:25]=1.C[Mg]Br>O1CCCC1>[ClH:1].[Cl:1][C:2]1[C:3]([C:26]([F:27])([F:28])[F:29])=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH:11]3[CH2:12][CH2:13][N:14]([C:17]4([CH3:23])[CH2:18][CH2:19][O:20][CH2:21][CH2:22]4)[CH2:15][CH2:16]3)[C:6]=2[CH:25]=1

参加物

4

反応物 2

HCID 598501594-{4-[6-Chloro-2-oxo-5-(trifluoromethyl)-2,3-dihydro-1H-benzimidazol-1-yl]-1-piperidinyl}tetrahydro-2H-pyran-4-carbonitrileHCID 178418573HCID 178418573、化合物

生成物 1

HCID 691279036-Chloro-1-[1-(4-methyltetrahydro-2H-pyran-4-yl)-4-piperidinyl]-5-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-one hydrochloride

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 4-{4-[6-chloro-2-oxo-5-(trifluoromethyl)-2,3-dihydro-1H-benzimidazol-1-yl]-1-piperidinyl}tetrahydro-2H-pyran-4-carbonitrile (D65, 1160 mg, 0.37 mmol) in tetrahydrofuran (5 ml) was treated with methylmagnesium bromide (3M in diethyl ether, 1.0 ml, 3.0 mmol). After 2 h at room temperature the solution was partitioned between aqueous Rochelle salt solution and dichloromethane, and the organic layer was dried (MgSO4) and evaporated The residue was chromatographed on silica gel eluting with methanol-dichloromethane mixtures to afford the title compound, which was isolated as the hydrochloride salt triturated from diethyl ether (110 mg). MH+=418 and 420,

後処理

  1. customAfter 2 h at room temperature the solution was partitioned between aqueous Rochelle salt solution and dichloromethane
  2. dry with materialthe organic layer was dried (MgSO4)
  3. customevaporated The residue
  4. customwas chromatographed on silica gel eluting with methanol-dichloromethane mixtures

出典と根拠

ORDレコード
ord-c2452bea3fac42b88d5063779ee0a739
出典データセット
uspto-grants-2012_10
特許番号
US08288412B2

反応ノート

読み込み中…