Hydrochloric Acid → 1-(1-{2-Chloro-4-[(1H-imidazol-2-ylmethyl)amino]phenyl}piperidin-4-yl)-1,4-dihydro-2H-3,1-benzoxazin-2-one

HRID 2414349노트

반응식

HRID 2414349 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[CH2:17][O:16][C:15]3=[O:24])[CH2:10][CH2:9]2)=[C:4]([Cl:25])[CH:3]=1.[NH:26]1[CH:30]=[CH:29][N:28]=[C:27]1[CH:31]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.C(=O)(O)[O-].[Na+]>CN1CCCC1=O.C(O)(=O)C>[Cl:25][C:4]1[CH:3]=[C:2]([NH:1][CH2:31][C:27]2[NH:26][CH:30]=[CH:29][N:28]=2)[CH:7]=[CH:6][C:5]=1[N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[CH2:17][O:16][C:15]2=[O:24])[CH2:12][CH2:13]1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 249551H-imidazole-2-carbaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 226446801-[1-(4-Amino-2-chlorophenyl)piperidin-4-yl]-1,4-dihydro-2H-3,1-benzoxazin-2-one

생성물 1

HCID 226446041-(1-{2-Chloro-4-[(1H-imidazol-2-ylmethyl)amino]phenyl}piperidin-4-yl)-1,4-dihydro-2H-3,1-benzoxazin-2-one

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

The product of example 120 step (ii) (0.25 g) was dissolved in 1-methyl-2-pyrrolidinone (6 ml) and this solution was treated with 2-imidazolecarboxaldehyde (0.1 g) followed by acetic acid (0.13 g) and then sodium triacetoxyborohydride (0.37 g). the reaction mixture was stirred at room temperature for three days. At the end of this time the mixture was poured in to excess aqueous dilute hydrochloric acid, this solution was allowed to stand for 10 minutes before being basified by addition of excess aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate, the organic layer was washed with water, dried and evaporated under reduced pressure. Purification was by chromatography eluting with methanol/chloroform (7/93). Yield 0.05 g as a solid.

후처리

  1. waitto stand for 10 minutes
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with water
  4. customdried
  5. customevaporated under reduced pressure
  6. customPurification
  7. washeluting with methanol/chloroform (7/93)

출처 및 근거

ORD 기록
ord-a7dad7f52af14945b026199abc48b266
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06812226B2

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