Chloroform → HCID 58406181, 화합물

HRID 221600노트

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HRID 221600 반응식
COC1C=CC(C[NH:8][C:9]2[C:14]3[N:15]=[C:16]4[N:21]([C:13]=3[C:12]([CH3:23])=[C:11]([CH3:24])[N:10]=2)[C@@H:20]([CH3:22])[CH2:19][O:18][CH2:17]4)=CC=1.[OH-].[Na+].C(Cl)(Cl)Cl>FC(F)(F)C(O)=O>[CH3:22][C@H:20]1[CH2:19][O:18][CH2:17][C:16]2=[N:15][C:14]3[C:9]([NH2:8])=[N:10][C:11]([CH3:24])=[C:12]([CH3:23])[C:13]=3[N:21]12

참가 물질

5

반응물 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 67156151HCID 67156151, 화합물

생성물 1

HCID 58406181HCID 58406181, 화합물수율 50%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

(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, 0.99 mmol) was dissolved in 15 mL of trifluoroacetic acid and stirred at ambient temperature overnight. The solvent was removed under reduced pressure to give an orange residue which was then treated with 30 mL of aqueous 10% NaOH solution and the mixture was stirred for 2 hours. The solution was then extracted with CH2Cl2 (3×30 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give an orange solid. Chromatography (SiO2, 10-30% CMA/CHCl3) gave an off-white solid. Crystallization from acetonitrile gave (4S)-4,6,7-trimethyl-3,4-dihydro-1H-pyrido[3′,4′:4,5]imidazo[2,1-c][1,4]oxazin-9-amine (115 mg) as a white powder, mp 264-267° C.

후처리

  1. customThe solvent was removed under reduced pressure
  2. customto give an orange residue which
  3. stirringthe mixture was stirred for 2 hours
  4. extractionThe solution was then extracted with CH2Cl2 (3×30 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give an orange solid
  10. customCrystallization from acetonitrile

출처 및 근거

ORD 기록
ord-caadab2dd26a4307b7de3141516a5242
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207162B2

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