Hydrochloric Acid → HCID 178509156, 화합물

HRID 2095167노트

반응식

HRID 2095167 반응식
[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

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 7923Maleic AnhydrideHCID 8471TriethylamineHCID 178510679HCID 178510679, 화합물

생성물 1

HCID 178509156HCID 178509156, 화합물수율 69.8%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d8b7a0bf981c4e2f843c281d63418d9e
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445694B2

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