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Triethylamine → N-(4-(4-(1-benzyl-2-(4-fluorophenylamino)-6-oxo-1,6-dihydropyrimidin-5-yl)-2-fluorophenoxy)pyridin-2-yl)pyrrolidine-1-carboxamide

HRID 2246478
ノート
印刷プレビュー

反応式

HRID 2246478 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[C:16](=[O:36])[N:17]([CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:18]([NH:21][C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)=[N:19][CH:20]=3)=[CH:11][C:10]=2[F:37])[CH:5]=[CH:4][N:3]=1.[CH3:38][CH2:39][N:40]([CH2:43][CH3:44])[CH2:41]C.ClC(OC1C=CC=CC=1)=[O:47].N1CCCC1>C1COCC1>[CH2:29]([N:17]1[C:16](=[O:36])[C:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:41]([N:40]4[CH2:43][CH2:44][CH2:38][CH2:39]4)=[O:47])[CH:7]=3)=[C:10]([F:37])[CH:11]=2)=[CH:20][N:19]=[C:18]1[NH:21][C:22]1[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 31268PyrrolidineHCID 592183715-(4-(2-aminopyridin-4-yloxy)-3-fluorophenyl)-3-benzyl-2-(4-fluorophenylamino)pyrimidin-4(3H)-one

生成物 1

HCID 59218374N-(4-(4-(1-benzyl-2-(4-fluorophenylamino)-6-oxo-1,6-dihydropyrimidin-5-yl)-2-fluorophenoxy)pyridin-2-yl)pyrrolidine-1-carboxamide収率 11.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

5-(4-(2-aminopyridin-4-yloxy)-3-fluorophenyl)-3-benzyl-2-(4-fluorophenylamino)pyrimidin-4(3H)-one (238 mg, 0.478 mmol) was dissolved in THF (4.0 ml) and Et3N (0.17 ml, 1220 μmol) and phenyl chloroformate (0.13 ml, 1.0 mmol) were added. The reaction was stirred under nitrogen, and after 40 minutes, pyrrolidine (0.60 ml, 7.2 mmol) was added. Stirring was continued at room temperature, until LCMS analysis indicated the formation of the product. The reaction was quenched with saturated ammonium chloride (10 ml) and extracted with DCM (3×20 ml). The organic extracts were combined, dried over sodium sulfate, filtered, concentrated, and purified on a silica gel column (30:1->20:1 DCM/MeOH). The fractions with product were collected, concentrated, and washed with Et2O and then with acetone. The suspension was filtered, and the solid was collected and dried in vacuo to afford the desired title compound N-(4-(4-(1-benzyl-2-(4-fluorophenylamino)-6-oxo-1,6-dihydropyrimidin-5-yl)-2-fluorophenoxy)pyridin-2-yl)pyrrolidine-1-carboxamide (33.2 mg, 0.0558 mmol, 4% over 3 steps). MS (ESI pos. ion) m/z: 595 (MH+). Calc'd exact mass for C33H25F2N6O3: 594. 1HNMR (400 MHz, CDCl3): 8.06 (d, J=6.4 Hz, 1H), 7.98 (s, 1H), 7.79 (d, J=1.2 Hz, 1H), 7.68 (dd, J=10.4 Hz, 2.0 Hz, 1H), 7.51-7.39 (m, 6H), 7.22 (t, J=8.0 Hz, 1H), 7.15 (dd, J=9.2 Hz, 5.2 Hz, 2H), 7.06-6.99 (m, 3H), 6.57 (dd, J=5.2 Hz, 3.2 Hz, 1H), 6.44 (s, 1H), 5.49 (s, 2H), 3.49-3.43 (m, 4H), 1.99-1.94 (m, 4H).

後処理

  1. stirringStirring
  2. customwas continued at room temperature, until LCMS analysis
  3. customThe reaction was quenched with saturated ammonium chloride (10 ml)
  4. extractionextracted with DCM (3×20 ml)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified on a silica gel column (30:1->20:1 DCM/MeOH)
  9. customThe fractions with product were collected
  10. concentrationconcentrated
  11. washwashed with Et2O
  12. filtrationThe suspension was filtered
  13. customthe solid was collected
  14. customdried in vacuo

出典と根拠

ORDレコード
ord-a5d4e9e49ce24f5f9ca41722f5291a00
出典データセット
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07687522B2

反応ノート

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