Guanidine Hydrochloride → HCID 10200445、化合物

HRID 2415111ノート

反応式

HRID 2415111 の反応式
[Br:1][C:2]1[C:11]2[C:6](=[C:7]([O:24][CH3:25])[CH:8]=[C:9]([CH2:12][C:13](=[CH:16]NC3C=CC=CC=3)[C:14]#[N:15])[CH:10]=2)[O:5][C:4]([CH3:27])([CH3:26])[CH:3]=1.Cl.[NH2:29][C:30]([NH2:32])=[NH:31].CC(C)([O-])C.[K+]>C(O)C>[Br:1][C:2]1[C:11]2[C:6](=[C:7]([O:24][CH3:25])[CH:8]=[C:9]([CH2:12][C:13]3[C:14]([NH2:15])=[N:31][C:30]([NH2:32])=[N:29][CH:16]=3)[CH:10]=2)[O:5][C:4]([CH3:27])([CH3:26])[CH:3]=1

参加物

5

反応物 3

HCID 5742Guanidine HydrochlorideHCID 23665647Potassium tert-butoxideHCID 69898773HCID 69898773、化合物

生成物 1

HCID 10200445HCID 10200445、化合物収率 48.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

The above prepared 418 mg of 2-(4-bromo-8-methoxy-2,2-dimethyl-2H-chromen-6-ylmethyl)-3-phenylamino-acrylonitrile were treated with 248 mg of guanidine hydrochloride (3.3 eq.), 291 mg of potassium-t-butoxide (3.3 eq.) and 16 ml of ethanol and heated under reflux under argon atmosphere for 14 hours. After cooling, the reaction mixture was poured onto crushed ice, extracted twice with AcOEt, washed with water and brine, dried over magnesium sulfate and evaporated to dryness. Flash chromatography (SiO2 with CH2Cl2/MeOH/25% NH3=19/1/0.05), followed by crystallization from EtOEt afforded 186 mg of the title compound as light-yellow crystals, mp.238-239°.

後処理

  1. temperatureheated
  2. temperatureunder reflux under argon atmosphere for 14 hours
  3. temperatureAfter cooling
  4. additionthe reaction mixture was poured
  5. customonto crushed ice
  6. extractionextracted twice with AcOEt
  7. washwashed with water and brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated to dryness
  10. customFlash chromatography (SiO2 with CH2Cl2/MeOH/25% NH3=19/1/0.05), followed by crystallization from EtOEt

出典と根拠

ORDレコード
ord-c54654863e464979ba5e29ba4c012c42
出典データセット
uspto-grants-2004_11
特許番号
US06818649B2

反応ノート

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