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

HRID 574206ノート

反応式

HRID 574206 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-97b7f44d02724de8bfd2fe07d2586e30
出典データセット
uspto-grants-2015_05
特許番号
US09034879B2

反応ノート

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