Hydrochloric Acid → HCID 178487686、化合物

HRID 2242449ノート

反応式

HRID 2242449 の反応式
C(O[K])CCC.[C:7]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=1[NH:18][C:19]([C:21]1[N:22]=[C:23]([NH:26][CH:27]([CH3:29])[CH3:28])[S:24][CH:25]=1)=O)(=[O:9])[CH3:8].[ClH:30]>C(O)CCC>[ClH:30].[CH:27]([NH:26][C:23]1[S:24][CH:25]=[C:21]([C:19]2[CH:8]=[C:7]([OH:9])[C:10]3[C:11](=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=3)[N:18]=2)[N:22]=1)([CH3:29])[CH3:28]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 11953491N-(2-Acetyl-5-methoxyphenyl)-2-((1-methylethyl)amino)-4-thiazolecarboxamideHCID 178454393potassium butan-1-olate

生成物 2

HCID 313Hydrochloric AcidHCID 178487686HCID 178487686、化合物収率 95.1%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

A solution of t.BuOK (2.42 g, 21 mmol) in anhydrous t.BuOH (40 mL) was heated to reflux. Compound 70 (1.8 g, 5.4 mmol) was added portion-wise over a 5 min period, and the dark red solution formed was stirred at reflux for an additional 20 min. The mixture was cooled to rt, and HCl (4 M in dioxane, 8.0 mL, 32 mmol) was added, after which the reaction mixture was concentrated under vacuum. In order to assure that all of the HCl and dioxane were removed, the crude product was re-dissolved in CH2Cl2 twice and thoroughly evaporated to obtain the slightly impure HCl salt of compound 71 (1.62 g) as a brown solid. The product was dissolved in CH2Cl2 and washed with saturated NaHCO3, after which the aqueous phase was extracted several times with CH2Cl2. The combined organic phases were dried (MgSO4) and evaporated to give compound 71 (1.38 g, 81%) as a light brown solid (>95% pure according to HPLC tests). 1H-NMR (MeOH-d4, 400 MHz): δ 1.30 (d, J=6.0 Hz, 6H), 3.93 (s, 3H), 3.95-4.07 (m, 1H), 6.73 (s, 1H), 6.99 (dd, J=2.4, 9.2 Hz, 1H), 7.26 (d, J=2.4 Hz, 1H), 7.37 (s, 1H), 8.10 (d, J=9.2 Hz, 1H).

後処理

  1. customthe dark red solution formed
  2. temperatureat reflux for an additional 20 min
  3. concentrationafter which the reaction mixture was concentrated under vacuum
  4. customwere removed
  5. dissolutionthe crude product was re-dissolved in CH2Cl2 twice
  6. customthoroughly evaporated

出典と根拠

ORDレコード
ord-0567cf24146c49869bb2047c6d8a36c3
出典データセット
uspto-grants-2010_03
特許番号
US07671032B2

反応ノート

読み込み中…