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Hydrochloric Acid → 1-(2,4-difluorophenyl)-3-(3-fluoro-4-(2-(5-((2-methoxyethylamino)methyl)-1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)urea

HRID 409980
ノート
印刷プレビュー

反応式

HRID 409980 の反応式
C(OC(=O)[N:7]([CH2:12][C:13]1[N:17]([CH3:18])[C:16]([C:19]2[S:27][C:26]3[C:21](=[N:22][CH:23]=[CH:24][C:25]=3[O:28][C:29]3[CH:34]=[CH:33][C:32]([NH:35][C:36]([NH:38][C:39]4[CH:44]=[CH:43][C:42]([F:45])=[CH:41][C:40]=4[F:46])=[O:37])=[CH:31][C:30]=3[F:47])[CH:20]=2)=[N:15][CH:14]=1)[CH2:8][CH2:9][O:10][CH3:11])(C)(C)C.Cl.O1CCOCC1.CCOC(C)=O>C(Cl)Cl.O.C([O-])(O)=O.[Na+]>[F:46][C:40]1[CH:41]=[C:42]([F:45])[CH:43]=[CH:44][C:39]=1[NH:38][C:36]([NH:35][C:32]1[CH:33]=[CH:34][C:29]([O:28][C:25]2[CH:24]=[CH:23][N:22]=[C:21]3[CH:20]=[C:19]([C:16]4[N:17]([CH3:18])[C:13]([CH2:12][NH:7][CH2:8][CH2:9][O:10][CH3:11])=[CH:14][N:15]=4)[S:27][C:26]=23)=[C:30]([F:47])[CH:31]=1)=[O:37]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 312751,4-DioxaneHCID 67049419tert-butyl(2-(7-(4-(3-(2,4-difluorophenyl)ureido)-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-1-methyl-1H-imidazol-5-yl)methyl(2-methoxyethyl)carbamate

生成物 1

HCID 579194881-(2,4-difluorophenyl)-3-(3-fluoro-4-(2-(5-((2-methoxyethylamino)methyl)-1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)urea
収率 61.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of 350 (600 mg, 0.879 mmol) in DCM (15 ml) was added HCl in dioxane (2 ml, 7.17 eq, 8 mmol, 4M in dioxane) and the reaction mixture was stirred at RT for 3 hours. The mixture wad diluted with water and solid NaHCO3 was added. The reaction mixture was extracted with EtOAc then the organic phase was collected, dried over Na2SO4, filtered and concentrated. Trituration of the residue with EtOAc afforded the desired compound 351 as an off-white solid (314 mg, 61% yield). 1H NMR (do-DMSO): 10.90 (s, 1H), 8.89 (s, 1H), 8.50 (d, J=5.48 Hz, 1H), 7.98 (m, 1H), 7.95 (s, 1H), 7.72 (m, 1H), 7.41 (m, 1H), 7.28-7.20 (m, 3H), 7.04 (m, 1H), 6.68 (d, J=5.28 Hz, 1H), 4.28 (s, 2H), 3.92 (s, 3H), 3.61 (m, 2H), 3.27 (s, 3H), 3.13 (m, 2H).

後処理

  1. additionwas added
  2. extractionThe reaction mixture was extracted with EtOAc
  3. customthe organic phase was collected
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-a030e78f658e4e248934ebb15cb117be
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08759522B2

反応ノート

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