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Trifluoroacetic acid → Ethyl 2-(4-(4-aminophenylthio)-3-(7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)benzamido)-2-phenylpropanoate

HRID 605411
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HRID 605411 반응식
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[CH:37]=[CH:36][C:19]([C:20]([NH:22][C:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([CH3:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:21])=[CH:18][C:17]=2[NH:38][C:39]2[C:40]3[CH:48]=[CH:47][C:46]([CH:49]([CH3:51])[CH3:50])=[N:45][C:41]=3[N:42]=[CH:43][N:44]=2)=[CH:11][CH:10]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][C:9]1[CH:10]=[CH:11][C:12]([S:15][C:16]2[CH:37]=[CH:36][C:19]([C:20]([NH:22][C:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([CH3:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:21])=[CH:18][C:17]=2[NH:38][C:39]2[C:40]3[CH:48]=[CH:47][C:46]([CH:49]([CH3:50])[CH3:51])=[N:45][C:41]=3[N:42]=[CH:43][N:44]=2)=[CH:13][CH:14]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 67040905Ethyl 2-(4-(4-(tert-butoxycarbonylamino)phenylthio)-3-(7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)benzamido)-2-phenylpropanoate

생성물 1

HCID 67041064Ethyl 2-(4-(4-aminophenylthio)-3-(7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)benzamido)-2-phenylpropanoate수율 84%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

The product of Example 444A (93 mg.) was reacted with trifluoroacetic acid [TFA] (0.60 mL) in dichloromethane (0.60 mL) added dropwise at room temperature then stirred at room temperature for 1 hour. The reaction mixture was concentrated and partitioned between ethyl acetate and saturated aqueous NaHCO3. The organic layer was washed with brine, dried over MgSO4, and concentrated. The residue was chromatographed on a C-18 HPLC column with a gradient elution of acetonitrile in 0.1% TFA water (0-100%). The desired fractions were combined, concentrated, dissolved in ethyl acetate, washed with saturated aqueous NaHCO3 then brine, dried over MgSO4 and concentrated to give a pale yellow amorphous solid (67 mg, 84%). 1H NMR (300 MHz, DMSO-D6) δ ppm 1.07 (t, J=6.99 Hz, 3 H) 1.34 (d, J=6.62 Hz, 6 H) 1.84 (s, 3 H) 3.15-3.29 (m, 1 H) 4.03 (q, J=7.35 Hz, 2 H) 5.59 (s, 2 H) 6.62 (d, J=8.46 Hz, 2 H) 6.84 (d, J=8.46 Hz, 1 H) 7.12 (d, J=8.46 Hz, 2 H) 7.24-7.41 (m, 4 H) 7.52 (d, J=7.35 Hz, 2 H) 7.63 (d, J=8.46 Hz, 1 H) 7.73 (dd, J=8.46, 1.84 Hz, 1 H) 7.90 (d, J=1.84 Hz, 1 H) 8.57 (s, 1 H) 8.83 (s, 1 H) 8.86 (d, J=8.46 Hz, 2 H) 10.13 (s, 1 H).

후처리

  1. additionadded dropwise at room temperature
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between ethyl acetate and saturated aqueous NaHCO3
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was chromatographed on a C-18 HPLC column with a gradient elution of acetonitrile in 0.1% TFA water (0-100%)
  8. concentrationconcentrated
  9. dissolutiondissolved in ethyl acetate
  10. washwashed with saturated aqueous NaHCO3
  11. dry with materialbrine, dried over MgSO4
  12. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a58c380e867b4b1883180a03d51075b3
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07910595B2

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