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Trifluoroacetic acid → HCID 73055151, 화합물

HRID 1778984
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HRID 1778984 반응식
[NH2:1][C:2](=[O:44])[CH2:3][C:4]1[CH:43]=[CH:42][CH:41]=[CH:40][C:5]=1[CH2:6][CH2:7][C:8]1[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][N:11]=[C:10]([NH:18][C:19]2[CH:39]=[CH:38][C:22]([C:23]([N:25]3[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]3)=[O:24])=[CH:21][CH:20]=2)[N:9]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl.C1CCCCC1>[N:25]1([C:23]([C:22]2[CH:21]=[CH:20][C:19]([NH:18][C:10]3[N:9]=[C:8]([CH2:7][CH2:6][C:5]4[CH:40]=[CH:41][CH:42]=[CH:43][C:4]=4[CH2:3][C:2]([NH2:1])=[O:44])[C:13]([C:14]([F:16])([F:15])[F:17])=[CH:12][N:11]=3)=[CH:39][CH:38]=2)=[O:24])[CH2:26][CH2:27][NH:28][CH2:29][CH2:30]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 6422Trifluoroacetic acidHCID 86712649tert-Butyl 4-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzoyl)piperazine-1-carboxylate

생성물 1

HCID 73055151HCID 73055151, 화합물수율 87%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8078Cyclohexane용매

실험 절차

To a solution of tert-butyl 4-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzoyl)piperazine-1-carboxylate (A26) (0.182 g, 0.297 mmol) in DCM (4 mL) was added TFA (1 mL) and the resulting mixture was stirred at room temperature for 16 hours. The volatiles were removed in vacuo and the residue partitioned between EtOAc (10 mL) and 2 M aqueous NaOH (10 mL). The aqueous layer was extracted with EtOAc (2×10 mL) then the combined organic fractions were washed with water (10 mL), brine (10 mL) and dried over MgSO4. The volatiles were removed in vacuo to give a yellow solid, which was suspended in cyclohexane and then filtered to give the title compound 6 as a white solid (0.132 g, 87%); 1H NMR (400 MHz, d4-MeOH) δ 8.62 (s, 1H), 7.83 (d, J=8.7 Hz, 2H), 7.42 (d, J=8.8 Hz, 2H), 7.27 (d, J=6.3 Hz, 1H), 7.23-7.15 (m, 3H), 3.68 (s, 2H), 3.82-3.46 (m, 4H), 3.23-3.15 (m, 2H), 3.12 (dd, J=9.8, 5.4 Hz, 2H), 3.02-2.71 (m, 4H). LCMS-A: rt 4.676 min; m/z 513.3 [M+H]+.

후처리

  1. customThe volatiles were removed in vacuo
  2. customthe residue partitioned between EtOAc (10 mL) and 2 M aqueous NaOH (10 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
  4. washthe combined organic fractions were washed with water (10 mL), brine (10 mL)
  5. dry with materialdried over MgSO4
  6. customThe volatiles were removed in vacuo
  7. customto give a yellow solid, which
  8. filtrationfiltered

출처 및 근거

ORD 기록
ord-eb3f008ac60e4015be2ef3c6aeaedf1a
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09266864B2

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