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Ammonium Chloride → HCID 86668505, 화합물

HRID 1805268
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HRID 1805268 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14](O)=[O:15])=[C:12]([C:17]2[CH:18]=[N:19][N:20]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=3)[C:21]=2[C:22]([F:25])([F:24])[F:23])[O:11][N:10]=1.[Cl-].[NH4+].CC([N:38](C)C)=O.CCN(C(C)C)C(C)C>C(OC(=O)C)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14]([NH2:38])=[O:15])=[C:12]([C:17]2[CH:18]=[N:19][N:20]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=3)[C:21]=2[C:22]([F:23])([F:25])[F:24])[O:11][N:10]=1
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참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 31374DimethylacetamideHCID 81531DiisopropylethylamineHCID 86668506HCID 86668506, 화합물

생성물 1

HCID 86668505HCID 86668505, 화합물

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Saponification of the ester of example I-11 was achieved following the description for example I-19, first step, to give 3-(2-chloro-6-fluorophenyl)-5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylic acid in 89% yield. To a solution of 6.0 g (12.34 mmol) 3-(2-chloro-6-fluorophenyl)-5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylic acid and 1.98 g (37.021 mmol) ammoniumchlorid in 20 mL dry DMA 9.36 g (24.681 mmol) HBTU and 6.45 mL (37.021 mmol) DIPEA were added. The mixture was stirred 3 hours at r.t. Ethylacetate was added to the reaction mixture and it was washed twice with sodium hydrogen carbonate (5%, aq) and citric acid (5%, aq). The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed in the vacuum. The oily residue became solid by drying in the vacuum. The solid was washed with petroleum ether, filtrated and dried in the vacuum to yield 5.37 g (90%) of example I-121. Result of LC/MS MH+: 484.83; 1H NMR (DMSO-d6; CCl4): 7.39-7.78 (7H, m, CH-arom./2H NH2), 8.43 (1H, s, CH-pyraz.)

후처리

  1. washwas washed twice with sodium hydrogen carbonate (5%, aq) and citric acid (5%, aq)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was removed in the vacuum
  4. customby drying in the vacuum
  5. washThe solid was washed with petroleum ether
  6. filtrationfiltrated
  7. customdried in the vacuum
  8. customto yield 5.37 g (90%) of example I-121
  9. customResult of LC/MS MH+

출처 및 근거

ORD 기록
ord-aa0e1154b36d42e6be38910dbf0b53c4
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08354436B2

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