Hydrochloric Acid → 8-Butyl-2-(2-methoxyphenyl)-5,6,7,8-tetrahydro-imidazo[1,2-a]pyrazine

HRID 639421ノート

反応式

HRID 639421 の反応式
[CH2:1]([C:5]1[C:6]2[N:7]([CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH3:22])[N:14]=2)[CH2:8][C:9](=O)[N:10]=1)[CH2:2][CH2:3][CH3:4].B.C1COCC1.Cl.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[CH2:1]([CH:5]1[NH:10][CH2:9][CH2:8][N:7]2[CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH3:22])[N:14]=[C:6]12)[CH2:2][CH2:3][CH3:4]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2723981Borane;tetrahydrofuranHCID 220168358-Butyl-6-oxo-2-(2-methoxyphenyl)-imidazo[1,2-a]pyrazine

生成物 1

HCID 220168108-Butyl-2-(2-methoxyphenyl)-5,6,7,8-tetrahydro-imidazo[1,2-a]pyrazine収率 92%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The product from Step 1.e. (6.13 g, 20.5 mmol) (compound vi where R3 is n-butyl, R4 is 2-methoxyphenyl, and R5 and R6 are H) was dissolved in THF (100 ml) and treated with 1M BH3/THF (82.0 ml, 82.0 mmol) at room temperature for about 2 hours and then refluxed for about 3 hours. The mixture was cooled to room temperature and 4N HCl (50 ml) was added dropwise. The mixture was stirred at room temperature for about 2 hours then made basic by careful portionwise addition of solid K2CO3. Product was extracted with EtOAc (3×50 ml). The EtOAc layers were combined, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was dissolved in MeOH (about 50 ml), concentrated HCl (1.75 ml) was added and the solution was again concentrated under reduced pressure. The product was crystallized from MeOH/Et2O to yield 6.76 g (92%) of the desired product. Mass spec. 286.3 MH+, NMR (300 MHz, DMSO-d6, 30° C.) 10.0-11.5 (2H, s broad), 8.05-8.15 (1H, d,d), 8.0-8.1 (1H, s), 7.35-7.5 (1H, t), 7.15-7.3 (1H, d), 7.0-7.15 (1H, t), 4.8-4.95 (1H, m), 4.4-4.65 (2H, m), 3.9-4.0 (3H, s), 3.65-3.8 (1H, m), 3.5-3.65 (1H, m), 2.45-2.65 (1H, m), 2.1-2.35 (1H, m), 1.5-1.7 (2H, m), 1.25-1.5 (2H, m), 0.85-1.0 (3H, t).

後処理

  1. temperaturerefluxed for about 3 hours
  2. extractionProduct was extracted with EtOAc (3×50 ml)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in MeOH (about 50 ml)
  7. additionconcentrated HCl (1.75 ml) was added
  8. concentrationthe solution was again concentrated under reduced pressure
  9. customThe product was crystallized from MeOH/Et2O

出典と根拠

ORDレコード
ord-37f8fbed6627418e9ac31b8223ffaff7
出典データセット
uspto-grants-2010_04
特許番号
US07691859B2

反応ノート

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