Chloroform → HCID 67156151、化合物

HRID 549167ノート

反応式

HRID 549167 の反応式
Cl[C:2]1[C:7]2[N:8]=[C:9]3[N:14]([C:6]=2[C:5]([CH3:16])=[C:4]([CH3:17])[N:3]=1)[C@@H:13]([CH3:15])[CH2:12][O:11][CH2:10]3.[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1.Cl.N1C=CC=CC=1.C(Cl)(Cl)Cl>FC(F)(F)CO>[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH:25][C:2]2[C:7]3[N:8]=[C:9]4[N:14]([C:6]=3[C:5]([CH3:16])=[C:4]([CH3:17])[N:3]=2)[C@@H:13]([CH3:15])[CH2:12][O:11][CH2:10]4)=[CH:22][CH:21]=1

参加物

6

反応物 4

HCID 6212ChloroformHCID 754524-MethoxybenzylamineHCID 10176127Pyridinium chlorideHCID 86624131HCID 86624131、化合物

生成物 1

HCID 67156151HCID 67156151、化合物収率 92.8%

試薬・触媒・溶媒 1

HCID 64092,2,2-Trifluoroethanol溶媒

反応条件

温度
160 °C

実験手順

A conical microwave vial was charged with a solution of (4S)-9-chloro-4,6,7-trimethyl-3,4-dihydro-1H-pyrido[3′,4′:4,5]imidazo[2,1-c][1,4]oxazine (270 mg, 1.07 mmol) dissolved in 3.5 mL of 2,2,2-trifluoroethanol. 4-Methoxybenzylamine (1.4 mL, 10.7 mmol) and pyridine hydrochloride (620 mg, 5.35 mmol) were added and the vial was sealed. The solution was heated in an Emrys Optimizer microwave (Personal Chemistry) at 160° C. for 120 minutes. The solvent was removed under reduced pressure, and the resulting residue was partitioned between 20 mL of CH2Cl2 and 20 mL of 10% aqueous Na2CO3. The layers were separated, and the organic portion was washed with 10% aqueous Na2CO3 solution and brine, dried over Na2SO4, filtered and concentrated under reduced pressures to give a crude oil. Chromatography (SiO2, 0-20% CMA/CHCl3) afforded (4S)—N-(4-methoxybenzyl)-4,6,7-trimethyl-3,4-dihydro-1H-pyrido[3′,4′:4,5]imidazo[2,1-c][1,4]oxazin-9-amine (350 mg) as an orange syrup.

後処理

  1. customthe vial was sealed
  2. customThe solvent was removed under reduced pressure
  3. customthe resulting residue was partitioned between 20 mL of CH2Cl2 and 20 mL of 10% aqueous Na2CO3
  4. customThe layers were separated
  5. washthe organic portion was washed with 10% aqueous Na2CO3 solution and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressures
  9. customto give a crude oil

出典と根拠

ORDレコード
ord-84021b4f78a44e8d8d88e10c53382685
出典データセット
uspto-grants-2011_05
特許番号
US07943609B2

反応ノート

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