Triethylamine → 2-(3,5-difluorophenyl)-N-[1-oxo-4-(trifluoromethyl)phthalazin-2(1H)-yl]acetamide

HRID 469530ノート

反応式

HRID 469530 の反応式
[NH2:1][N:2]1[N:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:16].C(N(CC)CC)C.[F:24][C:25]1[CH:26]=[C:27]([CH2:32][C:33](O)=[O:34])[CH:28]=[C:29]([F:31])[CH:30]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C=O)C.CCOC(C)=O>[F:24][C:25]1[CH:26]=[C:27]([CH2:32][C:33]([NH:1][N:2]2[N:11]=[C:10]([C:12]([F:15])([F:13])[F:14])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]2=[O:16])=[O:34])[CH:28]=[C:29]([F:31])[CH:30]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 1454243,5-Difluorophenylacetic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 671611112-amino-4-(trifluoromethyl)phthalazin-1(2H)-one

生成物 1

HCID 532370652-(3,5-difluorophenyl)-N-[1-oxo-4-(trifluoromethyl)phthalazin-2(1H)-yl]acetamide収率 7.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of the product of Example 11B (40.3 mg, 0.18 mmol), triethylamine (0.037 mL, 0.26 mmol), 2-(3,5-difluorophenyl)acetic acid (36.4 mg, 0.21 mmol), and O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (61.8 mg, 0.19 mmol) in DMF (0.75 mL) was stirred overnight, diluted with EtOAc, washed with 1 N NaOH and brine, dried (Na2SO4), and filtered. The residue was chromatographed on SiO2 (3% EtOAc/CH2Cl2) to give the title compound as a white solid (4.8 mg, 0.013 mmol). 1H NMR (300 MHz, DMSO-d6) δ 11.95 (s, 1H), 8.44 (d, 1H), 8.23-7.90 (m, 3H), 7.26-7.00 (m, 3H), 3.80 (s, 2H); MS (DCI) M/Z 401.2 (M+NH4)+.

後処理

  1. washwashed with 1 N NaOH and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customThe residue was chromatographed on SiO2 (3% EtOAc/CH2Cl2)

出典と根拠

ORDレコード
ord-bd3ed716e5274c06aa50dce9d5276f1a
出典データセット
uspto-grants-2014_01
特許番号
US08629143B2

反応ノート

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