Trifluoroacetic acid → HCID 178510239、化合物

HRID 1874910

反応式

HRID 1874910 の反応式
[Cl:1][C:2]1[N:3]=[CH:4][N:5](COCC[Si](C)(C)C)[C:6]=1[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][C:19]2[CH:24]=[C:23]([CH:25]3[CH2:27][CH2:26]3)[CH:22]=[C:21]([C:28]#[N:29])[CH:20]=2)[C:12]=1[F:30])=[O:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][C:19]2[CH:24]=[C:23]([CH:25]3[CH2:27][CH2:26]3)[CH:22]=[C:21]([C:28]#[N:29])[CH:20]=2)[C:12]=1[F:30])=[O:8]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 684876074-chloro-N-({4-chloro-3-[(3-cyano-5-cyclopropylphenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide

生成物 1

HCID 178510239HCID 178510239、化合物収率 68.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

4-chloro-N-({4-chloro-3-[(3-cyano-5-cyclopropylphenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (0.132 g, 0.230 mmol) was dissolved in DCM (3 mL) and treated with TFA (3 mL) at 25° C. for 3 days. The reaction mixture was concentrated to dryness and partitioned between DCM and saturated aqueous NaHCO3. The organic phase was isolated, dried over MgSO4, filtered and concentrated to dryness. The residue was purified on 40 g silica gel eluted with 0 to 10% CH3OH/DCM to give 4-chloro-N-({4-chloro-3-[(3-cyano-5-cyclopropylphenyl)oxy]-2-fluorophenyl}methyl)-1H-imidazole-5-carboxamide (0.0705 g, 0.158 mmol, 68.8% yield) as a white foam. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.19 (br. s., 1H), 8.26 (br. s., 1H), 7.78 (s, 1H), 7.31-7.55 (m, 2H), 7.27 (br. s., 1H), 7.09 (s, 2H), 4.53 (d, J=1.39 Hz, 2H), 1.91-2.07 (m, 1H), 0.99 (m, 2H), 0.77 (m, 2H). LC-MS (ES−) m/z 443.18, 445.11 [M−1]. LC-MS (ES+) m/z 445.07, 447.08 [M+H].

後処理

  1. concentrationThe reaction mixture was concentrated to dryness
  2. custompartitioned between DCM and saturated aqueous NaHCO3
  3. customThe organic phase was isolated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was purified on 40 g silica gel
  8. washeluted with 0 to 10% CH3OH/DCM

出典と根拠

ORDレコード
ord-08f84591f27046948471b93770e0d504
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

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