Hydrochloric Acid → [2-Chloro-4-(2,4-difluoro-phenylamino)-phenyl]-{5-[1-(2,3-dihydroxy-propyl)-1H-[1,2,3]triazol-4-yl]-2-methyl-phenyl}-methanone

HRID 2067199ノート

反応式

HRID 2067199 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])[CH:5]=[CH:4][C:3]=1[C:17]([C:19]1[CH:24]=[C:23]([C:25]2[N:26]=[N:27][N:28]([CH2:30][CH:31]3[CH2:35][O:34]C(C)(C)[O:32]3)[CH:29]=2)[CH:22]=[CH:21][C:20]=1[CH3:38])=[O:18].Cl.CCOC(C)=O>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])[CH:5]=[CH:4][C:3]=1[C:17]([C:19]1[CH:24]=[C:23]([C:25]2[N:26]=[N:27][N:28]([CH2:30][CH:31]([OH:32])[CH2:35][OH:34])[CH:29]=2)[CH:22]=[CH:21][C:20]=1[CH3:38])=[O:18]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 11497523HCID 11497523、化合物

生成物 1

HCID 11555090[2-Chloro-4-(2,4-difluoro-phenylamino)-phenyl]-{5-[1-(2,3-dihydroxy-propyl)-1H-[1,2,3]triazol-4-yl]-2-methyl-phenyl}-methanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of compound 105 (535 mg, 1.16 mmol) in THF (6.0 mL) was added aqueous HCl (1M, 6 mL)) and the mixture was stirred for 24 h at RT. The reaction mixture was poured into a mixture of EtOAc/saturated NaHCO3. The aqueous phase was washed with more EtOAc. The collected organic phases were washed with water, brine and then dried (MgSO4), filtered and concentrated in vacuo to give the crude product. The crude product was purified by continuous gradient flash chromatography using MeOH/DCM 2:98 to 10:90 as the eluent to afford the title compound as yellow foam. 13C NMR (DMSO-d6) δ 194.9, 158.7 (dd), 155.7 (dd), 149.3, 145.0, 139.8, 135.7, 133.7, 133.7, 131.6, 128.4, 127.1, 126.6, 126.5 (dd), 124.9, 124.2 (dd), 122.3, 114.8, 112.0 (dd), 111.8, 105.0 (dd), 70.3, 63.2, 53.0, 19.4

後処理

  1. washThe aqueous phase was washed with more EtOAc
  2. washThe collected organic phases were washed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give the crude product
  7. customThe crude product was purified by continuous gradient flash chromatography

出典と根拠

ORDレコード
ord-d22df564bb3a4125a4e96e71a6141f52
出典データセット
uspto-grants-2012_10
特許番号
US08293772B2

反応ノート

読み込み中…