Thiourea → HCID 59790146、化合物

HRID 30815ノート

反応式

HRID 30815 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N:12]=[C:13]=S.[NH2:15][C:16]1[CH:17]=[C:18]([CH:37]=[CH:38][C:39]=1[NH:40][CH3:41])[O:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:27](=[O:36])[CH2:28][N:29]2[CH2:33][CH2:32][CH2:31][CH:30]2[CH2:34][OH:35])[CH:21]=1.NC(N)=S>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[NH:12][C:13]1[N:40]([CH3:41])[C:39]2[CH:38]=[CH:37][C:18]([O:19][C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:27](=[O:36])[CH2:28][N:29]4[CH2:33][CH2:32][CH2:31][C@H:30]4[CH2:34][OH:35])[CH:21]=3)=[CH:17][C:16]=2[N:15]=1

参加物

5

反応物 3

HCID 2723790ThioureaHCID 34078242-Fluoro-5-(trifluoromethyl)phenyl isothiocyanateHCID 69008962N-[4-(3-Amino-4-methylamino-phenoxy)-pyridin-2-yl]-2-(2-hydroxymethyl-pyrrolidin-1-yl)-acetamide

生成物 1

HCID 59790146HCID 59790146、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

2-Fluoro-5-(trifluoromethyl)phenyl isothiocyanate was added to a solution of N-[4-(3-Amino-4-methylamino-phenoxy)-pyridin-2-yl]-2-(2-hydroxymethyl-pyrrolidin-1-yl)-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 magnesium sulfate and concentrated. The crude product was purified by reverse phase HPLC. MS: MH+=559.3.

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 magnesium sulfate
  8. concentrationconcentrated
  9. customThe crude product was purified by reverse phase HPLC

出典と根拠

ORDレコード
ord-9537ba05e58746278b0d1175ec8c6a4e
出典データセット
uspto-grants-2008_09
特許番号
US07423150B2

反応ノート

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