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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
ノート
印刷プレビュー

反応式

HRID 605411 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a58c380e867b4b1883180a03d51075b3
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07910595B2

反応ノート

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