Sodium Iodide → HCID 178443979、化合物

HRID 486086

反応式

HRID 486086 の反応式
[SH:1][C:2]1[NH:3][C:4]2[C:5]([N:10]=1)=[N:6][CH:7]=[CH:8][CH:9]=2.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[C:26]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=1[F:36])=[O:27]>CN(C)C=O.C(OCC)(=O)C>[F:36][C:30]1[CH:31]=[C:32]([F:35])[CH:33]=[CH:34][C:29]=1[NH:28][C:26](=[O:27])[N:25]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][S:1][C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[N:3]=1

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 10342005N-(5-bromopentyl)-N'-(2,4-difluorophenyl)-N-heptylureaHCID 178527819HCID 178527819、化合物

生成物 1

HCID 178443979HCID 178443979、化合物収率 100%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

Part B. A 100 mL flask was charged with 2-mercaptoimidazo[4,5-b]-pyridine (0.65 g, 0.0043 mol), sodium iodide (0.129 g, 0.00086 mol), and potassium carbonate (0.789 g, 0.00571 mol) in N,N-dimethylformamide (15 mL). A solution of N-(5-bromopentyl)-N-heptyl-N'-(2,4-difluorophenyl)urea (2.34 g, 0.00558 mol) in N,N-dimethylformamide (20 mL) was added and the mixture was heated to 60° C. under nitrogen atmosphere for 18 hours, then cooled and poured into ethyl acetate (100 mL). The ethyl acetate solution was washed with water (3×100 mL), dried over magnesium sulfate and concentrated. Purification by flash chromatography of the resulting residue afforded the product, which solidified upon standing overnight. The residue was recrystallized to afford the title compound (2.13 g, 0.0043 mol) as a viscous oil. 1H NMR (CDCl3) δ8.27 (dd,1H,J=5.2, 1.4 Hz), 8.06-7.98 (m,1H), 7.91 (dd,1H,J=7.9, 1.3 Hz), 7.18 (dd,1H,J=7.9, 4.9 Hz), 6.84-6.76 (m,1H), 6.49 (d,1H,J=3.3 Hz), 3.41-3.24 (m,6H), 1.94-1.84 (m,2H), 1.74-1.51 (m,6H), 1.35-1.23 (m,8H), 0.88 (t,3H,J=6.6 Hz).

後処理

  1. temperaturecooled
  2. washThe ethyl acetate solution was washed with water (3×100 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customPurification by flash chromatography of the resulting residue
  6. customafforded the product, which
  7. customThe residue was recrystallized

出典と根拠

ORDレコード
ord-7e27aa2317d24042b58255345e6a845c
出典データセット
uspto-grants-1994_03
特許番号
US05290801

関連ノート

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