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Triethylamine → HCID 68159047, 화합물

HRID 403190
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HRID 403190 반응식
[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH:21]4[CH2:23][CH:22]4[NH2:24])=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.CCN(CC)CC.Cl[C:35]([O:37][C:38]1[C:43]([CH3:44])=[CH:42][C:41]([CH3:45])=[CH:40][C:39]=1[CH3:46])=[O:36]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[F:26][C:2]([F:1])([F:25])[O:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH:21]4[CH2:23][CH:22]4[NH:24][C:35](=[O:36])[O:37][C:38]4[C:43]([CH3:44])=[CH:42][C:41]([CH3:45])=[CH:40][C:39]=4[CH3:46])=[CH:17][CH:16]=3)=[N:11]2)=[CH:8][CH:9]=1
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 11106338HCID 11106338, 화합물HCID 68158720HCID 68158720, 화합물

생성물 1

HCID 68159047HCID 68159047, 화합물수율 79%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane
용매

실험 절차

2-{4-[1-(4-trifluoromethoxyphenyl)-1H-[1,2,4]triazol-3-yl]phenyl}cyclopropylamine (46.0 mg, 0.13 mmol, 1.0 equiv) was dissolved in CH2Cl2 (0.55 mL) under N2. 4-Dimethylaminopyridine (DMAP; 0.8 mg, 0.006 mmol, 0.05 equiv) and Et3N (27 μL, 0.19 mmol, 1.5 equiv) were added, followed by mesityl chloroformate prepared above (33 mg, 0.17 mmol, 1.2 equiv). The reaction was stirred for 5 min and was then quenched with NaHCO3 (aq). The layers were separated, and the aqueous layer was extracted twice more with CH2Cl2. The combined organic extracts were concentrated, and the crude product was purified by silica gel chromatography (EtOAc-hexanes gradient) to afford the title compound as a white solid (53.0 mg, 79%): mp 199-202° C.; 1H NMR (400 MHz, CDCl3, data for major rotamer) δ 8.54 (s, 1H), 8.08 (d, J=8.3 Hz, 2H), 7.78 (d, J=9.0 Hz, 2H), 7.39 (d, J=0.7 Hz, 2H), 7.32-7.21 (m, 2H), 6.86 (s, 2H), 5.71-5.36 (m, 0.7H), 5.22-4.82 (m, 0.3H), 3.09-2.81 (m, 1H), 2.26 (s, 4H), 2.17 (s, 6H), 1.43-1.26 (m, 2H); ESIMS m/z 523 (M+H).

후처리

  1. customprepared above (33 mg, 0.17 mmol, 1.2 equiv)
  2. customwas then quenched with NaHCO3 (aq)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted twice more with CH2Cl2
  5. concentrationThe combined organic extracts were concentrated
  6. customthe crude product was purified by silica gel chromatography (EtOAc-hexanes gradient)

출처 및 근거

ORD 기록
ord-065e2968b13a491599309642b980c802
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08748340B2

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