Hydrochloric Acid → HCID 178509156、化合物

HRID 2095167ノート

反応式

HRID 2095167 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-d8b7a0bf981c4e2f843c281d63418d9e
出典データセット
uspto-grants-2013_05
特許番号
US08445694B2

反応ノート

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