Thiourea → N-[4-({2-[(3-tert-butylphenyl)amino]-1-methyl-1H-benzimidazol-5-yl}oxy)pyridin-2-yl]-2-(4-methylpiperidin-1-yl)acetamide

HRID 1963735ノート

反応式

HRID 1963735 の反応式
[N-]=[C:2]=S.[C:4]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([CH3:7])([CH3:6])[CH3:5].[NH2:14][C:15]1[CH:16]=[C:17]([CH:36]=[CH:37][C:38]=1NC)[O:18][C:19]1[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26](=[O:35])[CH2:27][N:28]2[CH2:33][CH2:32][CH:31]([CH3:34])[CH2:30][CH2:29]2)[CH:20]=1.[NH2:41][C:42]([NH2:44])=S>CO>[C:4]([C:8]1[CH:13]=[C:12]([NH:41][C:42]2[N:44]([CH3:2])[C:38]3[CH:37]=[CH:36][C:17]([O:18][C:19]4[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26](=[O:35])[CH2:27][N:28]5[CH2:29][CH2:30][CH:31]([CH3:34])[CH2:32][CH2:33]5)[CH:20]=4)=[CH:16][C:15]=3[N:14]=2)[CH:11]=[CH:10][CH:9]=1)([CH3:7])([CH3:6])[CH3:5]

参加物

5

反応物 3

HCID 2723790ThioureaHCID 59789988N-{4-[3-amino-4-(methylamino)phenoxy](2-pyridyl)}-2-(4-methylpiperidyl)acetamideHCID 178440816HCID 178440816、化合物

生成物 1

HCID 59790090N-[4-({2-[(3-tert-butylphenyl)amino]-1-methyl-1H-benzimidazol-5-yl}oxy)pyridin-2-yl]-2-(4-methylpiperidin-1-yl)acetamide

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

3-(tert-Butyl)benzenisothiocyanate was added to a solution of N-{4-[3-amino-4-(methylamino)phenoxy](2-pyridyl)}-2-(4-methylpiperidyl)acetamide in methanol. Reaction was stirred at room temperature for 15 hours. Thiourea formation was confirmed by LC/MS. Ferric chloride was added and the resulting mixture was stirred at room temperature for 4 hours. After cyclization was complete by LC/MS the reaction mixture was concentrated and aqueous sodium carbonate was added until basic pH. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water then brine, and dried over sodium sulfate and concentrated. The crude product was purified by reverse phase HPLC. MS: MH+=527.2.

後処理

  1. customReaction
  2. stirringthe resulting mixture was stirred at room temperature for 4 hours
  3. concentrationwas concentrated
  4. additionaqueous sodium carbonate was added until basic pH
  5. customThe reaction mixture was partitioned between ethyl acetate and water
  6. washThe organic layer was washed with water
  7. dry with materialbrine, and dried over sodium sulfate
  8. concentrationconcentrated
  9. customThe crude product was purified by reverse phase HPLC

出典と根拠

ORDレコード
ord-ece16306258b41dfb7681b4c0a795d14
出典データセット
uspto-grants-2013_04
特許番号
US08415382B2

反応ノート

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