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(Diethylamino)sulfur trifluoride → 5-(1-fluorocyclobutyl)-N-[2-(5-methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonylpropan-2-yl]-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridine-2-carboxamide

HRID 1480203
ノート
印刷プレビュー

反応式

HRID 1480203 の反応式
O[C:2]1([C:6]2[C:7]([O:28][C@@H:29]([CH3:34])[C:30]([F:33])([F:32])[F:31])=[CH:8][C:9]([C:12]([NH:14][C:15]([C:22]3[N:26]=[C:25]([CH3:27])[O:24][N:23]=3)([CH3:21])[CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])=[O:13])=[N:10][CH:11]=2)[CH2:5][CH2:4][CH2:3]1.CCN(S(F)(F)[F:41])CC>ClCCl>[F:41][C:2]1([C:6]2[C:7]([O:28][C@@H:29]([CH3:34])[C:30]([F:31])([F:32])[F:33])=[CH:8][C:9]([C:12]([NH:14][C:15]([C:22]3[N:26]=[C:25]([CH3:27])[O:24][N:23]=3)([CH3:21])[CH2:16][S:17]([CH3:20])(=[O:18])=[O:19])=[O:13])=[N:10][CH:11]=2)[CH2:3][CH2:4][CH2:5]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 902034235-(1-hydroxycyclobutyl)-N-[1-methyl-1-(5-methyl-1,2,4-oxadiazol-3-yl)-2-methylsulfonyl-ethyl]-4-[(1S)-2,2,2-trifluoro-1-methyl-ethoxy]pyridine-2-carboxamide

生成物 1

HCID 902043215-(1-fluorocyclobutyl)-N-[2-(5-methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonylpropan-2-yl]-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridine-2-carboxamide収率 44%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

反応条件

温度
0 °C

実験手順

To a solution of 5-(1-hydroxycyclobutyl)-N-[2-(5-methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonylpropan-2-yl]-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridine-2-carboxamide (example 126e, 21 mg, 41.5 μmol) in dry dichloromethane (200 μl) under an argon atmosphere cooled down to 0° C. was added DAST (10.0 mg, 8.22 μl, 62.2 μmol). The reaction mixture was stirred at 0° C. for 1 h and quenched by addition of a 2M aqueous solution of sodium carbonate. The bi-phasic mixture was stirred for 15 minutes and the organic phase was collected. The organic phase was evaporated down to dryness and the crude material was purified by preparative HPLC to yield the title compound (9.2 mg, 44%). MS (ESI, m/z): 509.5 (M+H+).

後処理

  1. customquenched by addition of a 2M aqueous solution of sodium carbonate
  2. stirringThe bi-phasic mixture was stirred for 15 minutes
  3. customthe organic phase was collected
  4. customThe organic phase was evaporated down to dryness
  5. customthe crude material was purified by preparative HPLC

出典と根拠

ORDレコード
ord-6ebcf35676fb46f08d6d1acf35091b32
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09409866B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート