Water → 6-Cyclopropylmethoxy-5-pyrrolidin-1-yl-pyridine-2-carboxylic acid {(S)-3-methyl-1-[(7-nitro-benzo[1,2,5]oxadiazol-4-ylamino)-methyl]-butyl}-amide

HRID 632424ノート

反応式

HRID 632424 の反応式
[NH2:1][CH2:2][C@@H:3]([NH:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[C:13]([O:22][CH2:23][CH:24]2[CH2:26][CH2:25]2)[N:12]=1)=[O:10])[CH2:4][CH:5]([CH3:7])[CH3:6].[N+:27]([C:30]1[C:35]2=[N:36][O:37][N:38]=[C:34]2[C:33](N)=[CH:32][CH:31]=1)([O-:29])=[O:28].O>C1COCC1>[CH3:7][CH:5]([CH3:6])[CH2:4][C@H:3]([NH:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)=[C:13]([O:22][CH2:23][CH:24]2[CH2:25][CH2:26]2)[N:12]=1)=[O:10])[CH2:2][NH:1][C:33]1[C:34]2=[N:38][O:37][N:36]=[C:35]2[C:30]([N+:27]([O-:29])=[O:28])=[CH:31][CH:32]=1

参加物

5

反応物 3

HCID 962WaterHCID 6018944-Amino-7-nitrobenzofurazanHCID 711057266-Cyclopropylmethoxy-5-pyrrolidin-1-yl-pyridine-2-carboxylic acid ((S)-1-aminomethyl-3-methyl-butyl)-amide

生成物 1

HCID 866748006-Cyclopropylmethoxy-5-pyrrolidin-1-yl-pyridine-2-carboxylic acid {(S)-3-methyl-1-[(7-nitro-benzo[1,2,5]oxadiazol-4-ylamino)-methyl]-butyl}-amide収率 57.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a colorless solution of 6-cyclopropylmethoxy-5-pyrrolidin-1-yl-pyridine-2-carboxylic acid ((S)-1-aminomethyl-3-methyl-butyl)-amide (30 mg, 83.2 μmol) in THF (555 μl) was added 7-nitro-2,1,3-benzoxadiazol-4-amine (CAN 10199-91-4, 19.9 mg, 100 μmol). The reaction mixture was stirred at room temperature for 30 minutes, followed by stirring at reflux temperature for 2 hours. After cooling to room temperature the mixture was poured into water (20 mL) and extracted with ethyl acetate (20 mL). The organic phase was washed with brine; and the aqueous phases were extracted with ethyl acetate. The organic phases were combined, dried with Na2SO4, and concentrated in vacuo. The black, solid residue was purified by flash chromatography (basic silica gel, 10 g, 0% to 100% ethyl acetate in a 1:1 mixture of dichloromethane and heptane) to give the title compound (25 mg, 57%) as brown solid; LC-MS (UV peak area/ESI) 100%, 524.2609 (M+H)+.

後処理

  1. stirringby stirring
  2. temperatureat reflux temperature for 2 hours
  3. temperatureAfter cooling to room temperature the mixture
  4. extractionextracted with ethyl acetate (20 mL)
  5. washThe organic phase was washed with brine
  6. extractionand the aqueous phases were extracted with ethyl acetate
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe black, solid residue was purified by flash chromatography (basic silica gel, 10 g, 0% to 100% ethyl acetate
  10. additionin a 1:1 mixture of dichloromethane and heptane)

出典と根拠

ORDレコード
ord-283590d2b73e4b7c90084f1f63f128d8
出典データセット
uspto-grants-2016_04
特許番号
US09321727B2

反応ノート

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