PyBroP → Tert-butyl 3-(2-((2,6-bis(trifluoromethyl)quinolin-4-yl)amino)acetamido)azetidine-1-carboxylate

HRID 1896834ノート

反応式

HRID 1896834 の反応式
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:12]=[C:11](O)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:4]=1.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH2:44][CH2:45][C:46]([NH:48][CH:49]1[CH2:52][N:51]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:50]1)=[O:47]>O1CCOCC1>[F:1][C:2]([F:19])([F:18])[C:3]1[CH:12]=[C:11]([NH:44][CH2:45][C:46]([NH:48][CH:49]2[CH2:52][N:51]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:50]2)=[O:47])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:4]=1

参加物

5

反応物 3

HCID 2733179PyBroPHCID 18699815Tert-butyl 3-(2-aminoacetamido)azetidine-1-carboxylateHCID 1785161332,6-Bis(trifluoromethyl)quinolin-4(1H)-one

生成物 1

HCID 86660461Tert-butyl 3-(2-((2,6-bis(trifluoromethyl)quinolin-4-yl)amino)acetamido)azetidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

実験手順

A solution of commercially available 2,6-bis(trifluoromethyl)quinolin-4-ol (291 mg, 1.04 mmol) in dry dioxane (5 mL) was treated sequentially with TEA (0.36 mL, 2.58 mmol) and PyBrOP (586 mg, 1.26 mmol). After stirring 1 hour at room temperature under argon, a solution of tert-butyl 3-(2-aminoacetamido)azetidine-1-carboxylate (352, 1.54 mmol), prepared as described in Example 1, Step E in dry dioxane (5 mL) was introduced and the reaction mixture was stirred overnight at room temperature. After concentration in vacuo, the residue was purified by flash chromatography (silica gel, 0-5% MeOH/ethyl acetate) to afford the product.

後処理

  1. additionwas introduced
  2. stirringthe reaction mixture was stirred overnight at room temperature
  3. concentrationAfter concentration in vacuo
  4. customthe residue was purified by flash chromatography (silica gel, 0-5% MeOH/ethyl acetate)
  5. customto afford the product

出典と根拠

ORDレコード
ord-eb44cbf949534acbac30b55cb8526b6e
出典データセット
uspto-grants-2013_08
特許番号
US08518969B2

反応ノート

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