Diisopropylethylamine → N-(4,4-difluorocyclohexyl)-8-nitroquinazolin-4-amine

HRID 1469729

反応式

HRID 1469729 の反応式
Cl[C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.[F:15][C:16]1([F:23])[CH2:21][CH2:20][CH:19]([NH2:22])[CH2:18][CH2:17]1.CCN(C(C)C)C(C)C>CC(O)C>[F:15][C:16]1([F:23])[CH2:21][CH2:20][CH:19]([NH:22][C:2]2[C:11]3[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][N:3]=2)[CH2:18][CH2:17]1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 3847030(4,4-Difluorocyclohexyl)amineHCID 114584714-Chloro-8-nitroquinazoline

生成物 1

HCID 71678050N-(4,4-difluorocyclohexyl)-8-nitroquinazolin-4-amine収率 61.2%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

A solution of 4-chloro-8-nitroquinazoline (Intermediate-7, step 2, 200 mg, 0.954 mmol), 4,4-difluorocyclohexanamine (491 mg, 2.86 mmol) and DIPEA (367 mg, 2.86 mmol) in iPrOH (2 mL) was heated in a sealed tube at 80° C. for 2 h. Then the reaction mixture was quenched with water at rt and was extracted with CHCl3. The organic layer was separated, dried, filtered and concentrated. The concentrate was purified by column chromatography using 3-5% EtOAc in CHCl3 to afford 180 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.59-8.55 (m, 2H), 8.43-8.40 (d, J=7.2 Hz, 1H), 8.27-8.25 (d, J=7.8 Hz, 1H), 7.69-7.63 (t, J=7.8 Hz, 1H), 4.41 (m, 1H), 2.26-2.00 (m, 6H), 1.75-1.71 (m, 2H); MS (m/z): 309.18 (M+H)+.

後処理

  1. customThen the reaction mixture was quenched with water at rt
  2. extractionwas extracted with CHCl3
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by column chromatography

出典と根拠

ORDレコード
ord-0921096d044e42d59ec9c1b94892f827
出典データセット
uspto-grants-2015_04
特許番号
US09006257B2

関連ノート

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