Diethyl Ether → (7R)-7-amino-4-chloro-9-(2,2,2-trifluoroethyl)-6,7,9,10-tetrahydroazepino[3,4-e]indazol-8(3H)-one

HRID 132449노트

반응식

HRID 132449 반응식
[Cl:1][C:2]1[C:10]2[NH:9][N:8]=[CH:7][C:6]=2[C:5]2[CH2:11][N:12]([CH2:28][C:29]([F:32])([F:31])[F:30])[C:13](=[O:27])[C@H:14]([NH:16]C(=O)OCC3C=CC=CC=3)[CH2:15][C:4]=2[CH:3]=1.C1(OC)C=CC=CC=1.CS(O)(=O)=O.C(OCC)C>ClCCl>[NH2:16][C@H:14]1[C:13](=[O:27])[N:12]([CH2:28][C:29]([F:30])([F:32])[F:31])[CH2:11][C:5]2[C:6]3[CH:7]=[N:8][NH:9][C:10]=3[C:2]([Cl:1])=[CH:3][C:4]=2[CH2:15]1

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 7519AnisoleHCID 59732091(R)-Benzyl 4-chloro-8-oxo-9-(2,2,2-trifluoroethyl)-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-ylcarbamate

생성물 1

HCID 59732089(7R)-7-amino-4-chloro-9-(2,2,2-trifluoroethyl)-6,7,9,10-tetrahydroazepino[3,4-e]indazol-8(3H)-one수율 78%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(R)-Benzyl 4-chloro-8-oxo-9-(2,2,2-trifluoroethyl)-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-ylcarbamate (450 mg, 964 μmol) was dissolved in dichloromethane (20 ml). Anisole (250 μl, 2300 μmol) was added to the mixture followed by methanesulfonic acid (5.0 ml, 77051 μmol). Reaction stirred at room temperature for 1.5 hours. 100 mL of diethyl ether was added to the mixture. Reaction stirred at room temperature for 45 minutes. Liquids were decanted off. Remaining solid was washed with diethyl ether and the liquids decanted. Solids were dissolved in water. Mixture was made basic with aqueous sodium bicarbonate. Mixture was extracted twice with ethyl acetate and the aqueous phase was discarded. Material was washed successively with aqueous sodium bicarbonate, water and brine and the aqueous phases were discarded. Organics were dried MgSO4, filtered and then concentrated to dryness. Title compound was obtained as light yellow solid in 78% yield. MS (M+H)+=321.2.

후처리

  1. customReaction
  2. customReaction
  3. stirringstirred at room temperature for 45 minutes
  4. customLiquids were decanted off
  5. washRemaining solid was washed with diethyl ether
  6. customthe liquids decanted
  7. dissolutionSolids were dissolved in water
  8. extractionMixture was extracted twice with ethyl acetate
  9. washMaterial was washed successively with aqueous sodium bicarbonate, water and brine
  10. filtrationfiltered
  11. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-0aac8d0fa60b467fbe7e50765304c2ef
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384931B2

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