Hydrochloric Acid → HCID 178509156、化合物

HRID 255001ノート

反応式

HRID 255001 の反応式
[NH2:1][CH2:2][C:3]1[C:4](=[N:9][NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[C:5]([NH2:8])=[N:6][N:7]=1.C(N(CC)CC)C.[C:25]1(=[O:31])[O:30][C:28](=[O:29])[CH:27]=[CH:26]1.Cl>CN(C=O)C.C(OCC)(=O)C>[NH2:8][C:5]1[C:4](=[N:9][NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[C:3]([CH2:2][NH:1][C:25]([CH:26]=[CH:27][C:28]([OH:30])=[O:29])=[O:31])=[N:7][N:6]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 7923Maleic AnhydrideHCID 8471TriethylamineHCID 178510679HCID 178510679、化合物

生成物 1

HCID 178509156HCID 178509156、化合物収率 69.8%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

5-Aminomethyl-4-[(3-fluorophenyl)hydrazono]-4H-pyrazol-3-ylamine (60 mg, 0.25 mmole) was dissolved in 3 mL of anhydrous DMF. To this solution was added triethylamine (0.51 mmole, 52 mg) and then a solution of maleic anhydride (30.2 mg, 0.31 mmole) in 1 mL of DMF. The reaction mixture was stirred at ambient temperature for 30 minutes and then worked up by the addition of saline and ethyl acetate. The mixture was acidified with 1 mL of 1.5 M HCl. The aqueous phase was extracted with ethyl acetate. The combined organic layer was washed with saline three times and dried over anhydrous MgSO4. The solution was then filtered, concentrated and purified by preparative TLC (CH2Cl2:MeOH:trace acetic acid=6:1) to yield 58 mg of the title compound as a yellow powder. MS (m/z, ES−): 331 (M−1, 100%); 1H NMR (ppm, 300 MHz, DMSO-d6) □δ 11.90 (br s, 1H), 7.35-7.70 (m, 3H), 7.30 (br s, 2H), 6.12 (d, 1H), 5.70 (d, 1H), 4.52 (s, 2H).

後処理

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. washThe combined organic layer was washed with saline three times
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationThe solution was then filtered
  5. concentrationconcentrated
  6. custompurified by preparative TLC (CH2Cl2:MeOH:trace acetic acid=6:1)

出典と根拠

ORDレコード
ord-2cc1dfe97ead4846b18c78deb40c361e
出典データセット
uspto-grants-2011_01
特許番号
US07875728B2

反応ノート

読み込み中…