Trifluoroacetic acid → [6-(6-Amino-3-aza-bicyclo[3.1.0]hex-3-yl)-pyrido[3,4-d]pyrimidin-4-yl]-[3-methyl-4-(pyridin-3-yloxy)-phenyl]-amine

HRID 584565ノート

反応式

HRID 584565 の反応式
C(OC(=O)[NH:7][CH:8]1[CH:13]2[CH:9]1[CH2:10][N:11]([C:14]1[N:38]=[CH:37][C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([O:29][C:30]5[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=5)=[C:25]([CH3:36])[CH:24]=4)[C:16]=3[CH:15]=1)[CH2:12]2)(C)(C)C.FC(F)(F)C(O)=O>>[NH2:7][CH:8]1[CH:9]2[CH:13]1[CH2:12][N:11]([C:14]1[N:38]=[CH:37][C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([O:29][C:30]5[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=5)=[C:25]([CH3:36])[CH:24]=4)[C:16]=3[CH:15]=1)[CH2:10]2

参加物

3

反応物 2

HCID 6422Trifluoroacetic acidHCID 11249486(3-{4-[3-Methyl-4-(pyridin-3-yloxy)-phenylamino]-pyrido[3,4-d]pyrimidin-6-yl}-3-aza-bicyclo[3.1.0]hex-6-yl)-carbamic acid tert-butyl ester

生成物 1

HCID 10224262[6-(6-Amino-3-aza-bicyclo[3.1.0]hex-3-yl)-pyrido[3,4-d]pyrimidin-4-yl]-[3-methyl-4-(pyridin-3-yloxy)-phenyl]-amine収率 98.8%

実験手順

A sample (0.26 g, 0.49 mmol) of (3-{4-[3-Methyl-4-(pyridin-3-yloxy)-phenylamino]-pyrido[3,4-d]pyrimidin-6-yl}-3-aza-bicyclo[3.1.0]hex-6-yl)-carbamic acid tert-butyl ester was treated with 0.5 mL of trifluoroacetic acid and immediately concentrated in vacuo. The residue was dissolved in chloroform and washed with saturated sodium bicarbonate. The aqueous layer was back extracted several times with chloroform. The organics were dried over sodium sulfate and evaporated to afford 206 mg of the title compound. A pure sample was obtained by crystallization from methanol and isopropyl ether. 1H NMR (CDCl3): δ 8.96 (s, 1), 8.53 (s, 1), 8.33 (m, 2), 7.65 (m, 1), 7.55 (m, 1), 7.21 (m, 2), 6.96 (d, 1), 615 (s, 1), 3.76 (d, 2), 3.54 (m, 2), 2.26 (s, 3), 2.24 (m, 1), 1.76 (m, 2). M.S. (m+1): 426. HPLC retention time (minutes): 3.919.

後処理

  1. concentrationimmediately concentrated in vacuo
  2. dissolutionThe residue was dissolved in chloroform
  3. washwashed with saturated sodium bicarbonate
  4. dry with materialThe organics were dried over sodium sulfate
  5. customevaporated

出典と根拠

ORDレコード
ord-2c0d8051515d4cd5bdc5ce467c99daf8
出典データセット
uspto-grants-2005_08
特許番号
US06927220B2

反応ノート

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