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Trifluoroacetic acid → HCID 67468650, 화합물

HRID 516690
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HRID 516690 반응식
FC(F)(F)C(O)=O.[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[NH:12][C:11](=[O:16])[C:10]=1[CH2:17][NH:18][C:19]([C:21]1[CH:29]=[C:28]([C:30]2[CH:31]=[CH:32][C:33]([N:36]3[CH2:41][CH2:40][N:39](C(OC(C)(C)C)=O)[CH2:38][C@H:37]3[CH3:49])=[N:34][CH:35]=2)[CH:27]=[C:26]2[C:22]=1[C:23]([CH3:53])=[CH:24][N:25]2[CH:50]([CH3:52])[CH3:51])=[O:20]>C(Cl)Cl>[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[NH:12][C:11](=[O:16])[C:10]=1[CH2:17][NH:18][C:19]([C:21]1[C:22]2[C:23]([CH3:53])=[CH:24][N:25]([CH:50]([CH3:52])[CH3:51])[C:26]=2[CH:27]=[C:28]([C:30]2[CH:35]=[N:34][C:33]([N:36]3[CH2:41][CH2:40][NH:39][CH2:38][C@H:37]3[CH3:49])=[CH:32][CH:31]=2)[CH:29]=1)=[O:20]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 68210133(R)-tert-Butyl 4-(5-(4-(((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamoyl)-1-isopropyl-3-methyl-1H-indol-6-yl)pyridin-2-yl)-3-methylpiperazine-1-carboxylate

생성물 1

HCID 67468650HCID 67468650, 화합물수율 52.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Added trifluoroacetic acid (1 ml, 12.98 mmol) to a solution of (R)-tert-butyl 4-(5-(4-(((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamoyl)-1-isopropyl-3-methyl-1H-indol-6-yl)pyridin-2-yl)-3-methylpiperazine-1-carboxylate (57 mg, 0.091 mmol) in DCM (3 mL) and let stir at RT for 1 hour. Concentrated on rotovap. Partitioned between DCM and sat′d Na2CO3, separated and washed DCM phase with water, brine, dried (MgSO4), filtered and rotovapped off DCM. Obtained 25 mg of the title compound as a tan solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.19 (d, 2H), 1.46-1.59 (m, 6H), 2.21 (s, 3H), 2.27 (s, 3H), 2.44 (s, 3H), 2.83 (dd, J=12.13, 3.54 Hz, 1H), 2.96-3.29 (m, 4H), 3.90 (br. s., 1H), 4.47-4.76 (m, 5H), 6.00 (s, 1H), 6.51 (d, J=8.59 Hz, 1H), 7.05 (s, 1H), 7.45 (s, 1H), 7.68 (dd, J=8.72, 2.40 Hz, 1H), 8.43 (d, J=2.27 Hz, 1H), 10.11-12.70 (m, 1H). LCMS: [M+H]+ 527.5.

후처리

  1. concentrationConcentrated on rotovap
  2. customPartitioned between DCM
  3. customseparated
  4. washwashed DCM phase with water, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered

출처 및 근거

ORD 기록
ord-7773a53d654f4f29bfe86349f56e6e03
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09114141B2

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