Picolinic acid → HCID 70247755、化合物

HRID 636286

反応式

HRID 636286 の反応式
[C:1]1([CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH2:8])[CH:2]=1.[CH:11]1[CH:12]=[CH:13][C:14]2N(O)N=[N:17][C:15]=2[CH:16]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27](O)=[O:28].CN([P+]([O:40]N1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[Na+].[Cl-]>CN(C=O)C.O.CCOC(C)=O>[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]([NH:8][CH2:7][C:3]1[CH:4]=[CH:5][CH:6]=[C:1]([CH2:9][NH:10][C:16](=[O:40])[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][N:17]=2)[CH:2]=1)=[O:28]

参加物

9

反応物 5

HCID 1018Picolinic acidHCID 5234Sodium ChlorideHCID 151331,3-BenzenedimethanamineHCID 757711-HydroxybenzotriazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

生成物 1

HCID 70247755HCID 70247755、化合物収率 103.6%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 1,3-xylylenediamine (132 uL, 1.00 mmol) in DMF (10 mL) was sequentially added IPr2NEt (1.75 mL, 10.0 mmol), HOBt (405 mg, 3.00 mmol), picolinic acid (370 mg, 3.00 mmol) and BOP reagent (1.33 g, 3.00 mmol). After 18 h at room temperature, the reaction mixture was added to a rapidly-stirred mixture of EtOAc (50 mL), H2O (50 mL), and sat'd NaCl (50 mL). After stirring for ca 1 h, the phases were separated and the aqueous layer was extracted with EtOAc (50 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to a brown oil. Purification by flash chromatography (silica gel, EtOAc) afforded 359 mg of the desired product as a white solid. MS (ES+) m/z 347.2 [M+H]+.

後処理

  1. customthe phases were separated
  2. extractionthe aqueous layer was extracted with EtOAc (50 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a brown oil
  6. customPurification by flash chromatography (silica gel, EtOAc)

出典と根拠

ORDレコード
ord-80ac522f774a415da7cfb328b872673e
出典データセット
uspto-grants-2001_02
特許番号
US06191146B1

関連ノート

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