Water → (R)-2-(5-bromo-4-cyano-2-fluorophenylamino)-3-methoxypropanamide

HRID 84852ノート

反応式

HRID 84852 の反応式
[Br:1][C:2]1[CH:9]=[C:8](F)[C:7]([F:11])=[CH:6][C:3]=1[C:4]#[N:5].Cl.[NH2:13][C@H:14]([CH2:18][O:19][CH3:20])[C:15]([NH2:17])=[O:16].CCN(C(C)C)C(C)C.O>CS(C)=O.CCOC(C)=O>[Br:1][C:2]1[C:3]([C:4]#[N:5])=[CH:6][C:7]([F:11])=[C:8]([NH:13][C@H:14]([CH2:18][O:19][CH3:20])[C:15]([NH2:17])=[O:16])[CH:9]=1

参加物

7

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 192612772-Bromo-4,5-difluorobenzonitrileHCID 86666156(R)-2-amino-3-methoxypropanamide hydrochloride

生成物 1

HCID 67508869(R)-2-(5-bromo-4-cyano-2-fluorophenylamino)-3-methoxypropanamide収率 21.4%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 2-bromo-4,5-difluorobenzonitrile (168 mg, 0.770 mmol), (R)-2-amino-3-methoxypropanamide hydrochloride (120 mg, 0.776 mmol) and DIEA (0.500 mL, 2.87 mmol) in DMSO (3 mL) was stirred at 120 C for 18 h. Water and EtOAc were added. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, which was eluted with 0-70% EtOAc in hexane to give (R)-2-(5-bromo-4-cyano-2-fluorophenylamino)-3-methoxypropanamide (52 mg).

後処理

  1. customThe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by a silica gel column, which
  5. washwas eluted with 0-70% EtOAc in hexane

出典と根拠

ORDレコード
ord-23dd50fad26047ad9ff9f271e7b546e0
出典データセット
uspto-grants-2014_09
特許番号
US08846928B2

反応ノート

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