Phenylacetic Acid → 3-Amino-6-bromo-N'-(2-phenylacetyl)-5-(trifluoromethyl)picolinohydrazide

HRID 574206노트

반응식

HRID 574206 반응식
[NH2:1][C:2]1[C:3]([C:13]([NH:15][NH2:16])=[O:14])=[N:4][C:5]([Br:12])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[C:17]1([CH2:23][C:24](O)=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN1C(=O)CCC1.CCOC(C)=O>[NH2:1][C:2]1[C:3]([C:13]([NH:15][NH:16][C:24](=[O:25])[CH2:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])=[N:4][C:5]([Br:12])=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

참가 물질

7

반응물 4

HCID 999Phenylacetic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 867295953-Amino-6-bromo-5-(trifluoromethyl)picolinohydrazide

생성물 1

HCID 867295943-Amino-6-bromo-N'-(2-phenylacetyl)-5-(trifluoromethyl)picolinohydrazide

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

To a stirred solution of 3-amino-6-bromo-5-(trifluoromethyl)picolinohydrazide (Int. H) (150 mg, 0.502 mmol) in NMP (4 ml) was added phenylacetic acid (57 mg, 0.419 mmol) followed by DIPEA (366 ul, 2.093 mmol). To this solution was added HATU (239 mg, 0.628 mmol) portionwise and the reaction mixture was left to stir at RT for 1 h. The reaction mixture was added to EtOAc (25 ml) and the organic portion was separated and washed with 0.1M HCl (2×15 ml), water (25 ml), 0.1M NaOH (2×15 ml), water (25 ml), brine (25 ml) dried (Mg SO4) and concentrated in vacuo. The crude product was purified by chromatography on silica eluting with 1:1 EtOAc/iso-hexane to afford the title compound as a yellow solid; 1H NMR (400 MHz, DMSO-d6) δ 10.30 (1H, s), 10.20 (1H, s), 7.70 (1H, s), 7.38 (4H, m), 7.25 (3H, m), 3.55 (2H, s). LC-MS Rt=1.43 min [M+H]+ 417.1 Method 2minLC_v002.

후처리

  1. waitthe reaction mixture was left
  2. customthe organic portion was separated
  3. washwashed with 0.1M HCl (2×15 ml), water (25 ml), 0.1M NaOH (2×15 ml), water (25 ml), brine (25 ml)
  4. dry with materialdried (Mg SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by chromatography on silica eluting with 1:1 EtOAc/iso-hexane

출처 및 근거

ORD 기록
ord-97b7f44d02724de8bfd2fe07d2586e30
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034879B2

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