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Trifluoroacetic acid → HCID 57897277, 화합물

HRID 416790
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HRID 416790 반응식
[CH3:1][C:2]1[CH:6]=[C:5]([NH:7][C:8](=[O:23])[CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16](OC(C)(C)C)=O)[CH2:12][CH2:11]2)[O:4][N:3]=1.C(O)(C(F)(F)F)=O.[NH2:31][C:32]1[C:37]([N+:38]([O-:40])=[O:39])=C(Cl)[C:35]([Cl:42])=[CH:34][N:33]=1.C(N(C(C)C)CC)(C)C>ClCCl.C(O)(C)C>[NH2:31][C:32]1[C:37]([N+:38]([O-:40])=[O:39])=[C:16]([N:13]2[CH2:12][CH2:11][N:10]([CH2:9][C:8]([NH:7][C:5]3[O:4][N:3]=[C:2]([CH3:1])[CH:6]=3)=[O:23])[CH2:15][CH2:14]2)[C:35]([Cl:42])=[CH:34][N:33]=1
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참가 물질

7

반응물 4

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 468676602-Amino-4,5-dichloro-3-nitropyridineHCID 57897266HCID 57897266, 화합물

생성물 1

HCID 57897277HCID 57897277, 화합물

시약·촉매·용매 2

HCID 3776Isopropanol용매2회
HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl 4-(2-(3-methylisoxazol-5-ylamino)-2-oxoethyl)piperazine-1-carboxylate (0.087 g, 0.27 mmol) in anhydrous dichloromethane (3 ml) was added TFA (3.7 ml). The reaction mixture was stirred at room temperature for 1 h and 45 min, then the solvent was removed in vacuo and the residue was dried in vacuo over P2O5. To a solution of this material (supposedly 0.27 mmol) in isopropanol (5 ml) was added 2-amino-4,5-dichloro-3-nitro-pyridine (0.050 g, 0.24 mmol) followed by diisopropylethylamine (0.22 ml, 1.25 mmol). The reaction mixture was stirred at 45° C. for 18 h, then allowed to cool to room temperature, and diluted with isopropanol (6 ml). The precipitate was collected by filtration, washed with isopropanol (2×6 ml), and diethyl ether (2×6 ml), and dried. The title compound was obtained as an orange solid (0.042 g). The filtrate was concentrated in vacuo, and purification of the residue by chromatography (10 g isolute column) on elution with dichloromethane/ethyl acetate (v/v; 1:1), and 2% methanol in dichloromethane/ethyl acetate (v/v; 1:1) afforded an additional 0.025 g of the product (overall yield: 63%). 1H-NMR (500 MHz, DMSO-d6) 2.18 (s, 3H, CH3), 2.63 (s, 4H, piperazine N(CH2)2), 3.28 (s, 2H, NCH2CO), 3.10 (s, 4H, piperazine N(CH2)2), 6.15 (s, 1H, isoxazole C—H), 7.00 (s, 2H, NH2), 8.07 (s, 1H, 6-H), 11.37 (s, 1H, CONH);

후처리

  1. customthe solvent was removed in vacuo
  2. dry with materialthe residue was dried in vacuo over P2O5
  3. stirringThe reaction mixture was stirred at 45° C. for 18 h
  4. temperatureto cool to room temperature
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with isopropanol (2×6 ml), and diethyl ether (2×6 ml)
  7. customdried

출처 및 근거

ORD 기록
ord-7b1741a8d35c48b3b0c51d6c917536a7
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08088761B2

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