Triethylamine → [4-(1H-benzimidazol-2-yl)piperidin-1-yl](5-bromopyridin-2-yl)methanone

HRID 1913150ノート

反応式

HRID 1913150 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.Cl.Cl.[NH:13]1[CH2:18][CH2:17][CH:16]([C:19]2[NH:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[N:20]=2)[CH2:15][CH2:14]1.Cl.C(N=C=N)C.C(N(CC)CC)C>ClC(Cl)C.CN(C)C1C=CN=CC=1>[NH:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=[C:19]1[CH:16]1[CH2:17][CH2:18][N:13]([C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)=[O:10])[CH2:14][CH2:15]1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 6085445-Bromopyridine-2-carboxylic acidHCID 21883477Ethylcarbodiimide hydrochlorideHCID 450738062-(piperidin-4-yl)-1H-benzimidazole dihydrochloride

生成物 1

HCID 58494556[4-(1H-benzimidazol-2-yl)piperidin-1-yl](5-bromopyridin-2-yl)methanone収率 14%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 63651,1-Dichloroethane溶媒

実験手順

To a stirred mixture of 5-bromopyridine-2-carboxylic acid (177 mg, 0.88 mmol) and 2-(piperidin-4-yl)-1H-benzimidazole dihydrochloride (200 mg, 0.73 mmol) in dichloroethane (5 mL) is added ethylcarbodiimide hydrochloride (168 mg, 0.88 mmol), triethylamine (0.25 mL, 1.82 mmol) and 4-dimethylaminopyridine (44.6 mg, 0.36 mmol). After 3 h the reaction mixture is washed with saturated aqueous NaHCO3, water and brine. The organic layer is dried over Na2SO4, filtered and concentrated under reduced pressure. Trituration from hot EtOAc gives 39.4 mg of [4-(1H-benzimidazol-2-yl)piperidin-1-yl](5-bromopyridin-2-yl)methanone.

後処理

  1. washAfter 3 h the reaction mixture is washed with saturated aqueous NaHCO3, water and brine
  2. dry with materialThe organic layer is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-2f0ceccfa4b24f44ad7d7b34e5f88c48
出典データセット
uspto-grants-2013_12
特許番号
US08609696B2

反応ノート

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