Hydrogen Bromide → 5-Cyclobutyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid [2-methanesulfonyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide

HRID 1480191ノート

反応式

HRID 1480191 の反応式
[CH:1]1([C:5]2[C:6]([O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:7][C:8]([C:11]([OH:13])=O)=[N:9][CH:10]=2)[CH2:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:51][C:52]1[O:56][N:55]=[C:54]([C:57]([NH2:64])([CH3:63])[CH2:58][S:59]([CH3:62])(=[O:61])=[O:60])[N:53]=1.Br>CN(C=O)C>[CH:1]1([C:5]2[C:6]([O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:7][C:8]([C:11]([NH:64][C:57]([CH3:63])([C:54]3[N:53]=[C:52]([CH3:51])[O:56][N:55]=3)[CH2:58][S:59]([CH3:62])(=[O:61])=[O:60])=[O:13])=[N:9][CH:10]=2)[CH2:2][CH2:3][CH2:4]1

参加物

7

反応物 5

HCID 260Hydrogen BromideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 902034302-(5-Methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonyl-propan-2-amineHCID 902048685-Cyclobutyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid

生成物 1

HCID 762847535-Cyclobutyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid [2-methanesulfonyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide収率 29%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 5-Cyclobutyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (example 108f, 40 mg, 145 μmol) in dry DMF (1.00 ml) was added DIEA (76.2 μl, 436 μmol) and TBTU (49.0 mg, 153 μmol) and the reaction mixture was stirred at room temperature for 20 minutes. Addition of 2-(5-methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonyl-propan-2-amine;hydrobromide (enantiomer B) (example 125b, 45.8 mg, 153 μmol) to the reaction mixture and the latter was stirred at room temperature for 2 hours. The crude was directly purified by preparative HPLC without any work-up to yield the title compound (20 mg, 29%); MS (ESI, m/z): 477.5 (M+H+).

後処理

  1. customThe crude was directly purified by preparative HPLC without any work-up

出典と根拠

ORDレコード
ord-d26de9262d73487ba08c6ec7b00251f9
出典データセット
uspto-grants-2016_08
特許番号
US09409866B2

反応ノート

読み込み中…