Dimethylformamide → 5-(1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl)-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-3-carbonitrile

HRID 1852979ノート

反応式

HRID 1852979 の反応式
[CH:1]1([CH:4]([N:8]2[CH:12]=[C:11]([C:13]3[N:18]4[C:19](I)=[CH:20][N:21]=[C:17]4[CH:16]=[C:15]([C:23]4[CH:24]=[N:25]N(C)[CH:27]=4)[N:14]=3)[CH:10]=[N:9]2)[CH2:5][C:6]#[N:7])[CH2:3][CH2:2]1.[C:29]([Cu])#[N:30].[CH3:32][N:33](C=O)C>CCOC(C)=O.[NH4+].[OH-]>[C:6]([CH2:5][CH:4]([N:8]1[CH:12]=[C:11]([C:13]2[N:18]3[C:19]([C:32]#[N:33])=[CH:20][N:21]=[C:17]3[CH:16]=[C:15]([C:23]3[CH:24]=[N:25][N:30]([CH3:29])[CH:27]=3)[N:14]=2)[CH:10]=[N:9]1)[CH:1]1[CH2:3][CH2:2]1)#[N:7]

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 866853053-cyclopropyl-3-(4-(3-iodo-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrileHCID 178418546HCID 178418546、化合物

生成物 1

HCID 674587565-(1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl)-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-3-carbonitrile収率 62%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 14923Ammonium Hydroxide溶媒

反応条件

温度
160 °C

実験手順

In a microwave safe flask, 3-cyclopropyl-3-(4-(3-iodo-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile (22.4 mg, 0.0463 mmol) and cyanocopper (4.56 mg, 0.0509 mmol) were suspended in DMF (463 μL, 0.0463 mmol). The reaction mixture was heated at 160° C. for 1 hour. The reaction mixture was cooled and diluted in EtOAc and 10% NH4OH (10 mL). The mixture was separated and the aqueous layer extracted with EtOAc. The combined organic layers were washed with brine, dried with MgSO4, filtered and concentrated in vacuo. Purification using preparative TLC in 15% MeOH/EtOAc afforded 5-(1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl)-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-3-carbonitrile (11.0 mg, 62.0% yield). MS (apci) m/z=384.4 (M+H).

後処理

  1. temperatureThe reaction mixture was cooled
  2. customThe mixture was separated
  3. extractionthe aqueous layer extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification

出典と根拠

ORDレコード
ord-caaf61609c6c499aacf504f0bceee1fe
出典データセット
uspto-grants-2015_02
特許番号
US08962596B2

反応ノート

読み込み中…