Hydrochloric Acid → 5-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-((1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)methyl)indolizine-8-carboxamide

HRID 1037095노트

반응식

HRID 1037095 반응식
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:25][C:26]1[CH:27]=[C:28]([C:34]2([C:51]([F:54])([F:53])[F:52])[O:38][N:37]=[C:36]([C:39]3[N:40]4[C:44]([C:45]([C:48](O)=[O:49])=[CH:46][CH:47]=3)=[CH:43][CH:42]=[CH:41]4)[CH2:35]2)[CH:29]=[C:30]([Cl:33])[C:31]=1[F:32].Cl.[NH2:56][CH2:57][C:58]1[CH:69]=[CH:68][C:61]2[B:62]([OH:67])[O:63][C:64]([CH3:66])([CH3:65])[C:60]=2[CH:59]=1.Cl>CC#N>[Cl:33][C:30]1[CH:29]=[C:28]([C:34]2([C:51]([F:53])([F:54])[F:52])[O:38][N:37]=[C:36]([C:39]3[N:40]4[C:44]([C:45]([C:48]([NH:56][CH2:57][C:58]5[CH:69]=[CH:68][C:61]6[B:62]([OH:67])[O:63][C:64]([CH3:66])([CH3:65])[C:60]=6[CH:59]=5)=[O:49])=[CH:46][CH:47]=3)=[CH:43][CH:42]=[CH:41]4)[CH2:35]2)[CH:27]=[C:26]([Cl:25])[C:31]=1[F:32]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86685451HCID 86685451, 화합물HCID 866855275-(5-(3,5-Dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-8-carboxylic acid

생성물 1

HCID 715765255-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-((1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)methyl)indolizine-8-carboxamide

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

HATU (350 mg, 0.92 mmol) can be added to CH3CN (5 mL) at 0° C. After stirring for 5 min, the mixture can be added to a solution of 5-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-8-carboxylic acid (0.46 mmol), 5-(aminomethyl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol hydrochloride (157 mg, 0.69 mmol), and TEA (186 mg, 1.83 mmol) in CH3CN (8 mL). Then the solution can be stirred at rt for 2 h. The solution can be acidified with HCl (1 N) and extracted with EA. The combined organic layers can be washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue can be purified by prep-TLC to give the final title compound.

후처리

  1. stirringThen the solution can be stirred at rt for 2 h
  2. extractionextracted with EA
  3. washThe combined organic layers can be washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue can be purified by prep-TLC

출처 및 근거

ORD 기록
ord-f57fde1e112f4daeb5b0ec7aea9ad374
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546357B2

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