Dimethylformamide → tert-butyl 6-amino-7-(cyclohexylethynyl)-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl(methyl)carbamate

HRID 17115

反応式

HRID 17115 の反応式
[C:1]([O:5][C:6](=[O:21])[N:7]([C:9]1[C:14]2[N:15]=[CH:16][N:17]([CH3:18])[C:13]=2[C:12](I)=[C:11]([NH2:20])[N:10]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[C:22]([CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)#[CH:23].C(NC(C)C)(C)C.CN(C)C=O>C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[NH2:20][C:11]1[N:10]=[C:9]([N:7]([CH3:8])[C:6](=[O:21])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:14]2[N:15]=[CH:16][N:17]([CH3:18])[C:13]=2[C:12]=1[C:23]#[C:22][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 70263Ethynylcyclohexane2 回HCID 46894439tert-Butyl (6-amino-7-iodo-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)(methyl)carbamate

生成物 1

HCID 60133861tert-butyl 6-amino-7-(cyclohexylethynyl)-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl(methyl)carbamate

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
95 °C

実験手順

A1.12 tert-Butyl-6-amino-7-iodo-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl(methyl)carbamate (1.0 g, 2.48 mmol), dichlorobis(triphenylphosphine)palladium (75 mg, 0.11 mmol), ethynylcyclohexane (0.3 g, 2.8 mmol), CuI (25 mg, 0.13 mmol), and diisopropylamine (5 mL) were added to N,N-dimethylformamide (7 mL). The reaction mixture was heated at 95° C. (in preheated oil bath) for 60 min. Additional ethynylcyclohexane (0.3 g, 2.8 mmol) was added to the reaction mixture and heated for another 60 min. The reaction was cooled and diluted with ethyl acetate and washed several times with water. The solvent removed under reduced pressure and the residue was chromatographed on a silica gel column (50%-70% ethyl acetate/hexane) to give 400 mg of C32.1 as a yellow solid. LCMS B: Ret time 3.15 min, (M+H)+=384.41.

後処理

  1. temperatureheated for another 60 min
  2. temperatureThe reaction was cooled
  3. washwashed several times with water
  4. customThe solvent removed under reduced pressure
  5. customthe residue was chromatographed on a silica gel column (50%-70% ethyl acetate/hexane)
  6. customto give 400 mg of C32.1 as a yellow solid
  7. customRet time 3.15 min, (M+H)+=384.41

出典と根拠

ORDレコード
ord-341fd1ab3d2e4c00a3d6c4f0fed9f36d
出典データセット
uspto-grants-2010_06
特許番号
US07737279B2

関連ノート

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