Water → HCID 66876386、化合物

HRID 631621

反応式

HRID 631621 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:10](=[O:13])([O-])[O-].[Cs+].[Cs+].Cl[C:17]1[N:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1.O.CN([CH:31]=[O:32])C>>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([O:9][C:25]2[C:24]3[C:19](=[CH:20][C:21]([O:13][CH3:10])=[C:22]([O:32][CH3:31])[CH:23]=3)[N:18]=[CH:17][N:26]=2)=[CH:3][C:2]=1[NH2:1]

参加物

6

反応物 5

HCID 962WaterHCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 740542-ChloroquinazolineHCID 50700783-Amino-4-chlorophenol

生成物 1

HCID 66876386HCID 66876386、化合物

実験手順

A solution of 3-amino-4-chlorophenol (1.00 g, 7.0 mmol) and cesium carbonate (3.38 g, 10.4 mmol) in DMF (20 mL) were heated at 80 C for 1 hr. The chloroquinazoline (1.61 g, 7.2 mmol) was added and the mixture heated for an additional hour. The mixture was poured into water (300 mL) and extracted with EtOAc twice. The combined extracts were washed with brine, dried with magnesium sulfate, filtered and concentrated. The residue was purified using silica gel chromatography eluting with EtOAc/hexane (30-70%), the main peak collected and triturated with DCM to afford 2-chloro-5-(6,7-dimethoxyquinazolin-4-yloxy)aniline. 1H NMR (300 MHz, DMSO d6) δ 3.96 (s, 6H), 5.55 (s, 2H), 6.45 (t, 1H), 6.76 (d, 1H), 7.25 (d, 1H), 7.36 (s, 1H), 7.50 (s, 1H), 8.55 (s, 1H); LC-MS (ESI) m/z 332 (M+H)+

後処理

  1. temperaturethe mixture heated for an additional hour
  2. extractionextracted with EtOAc twice
  3. washThe combined extracts were washed with brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified
  8. washeluting with EtOAc/hexane (30-70%)
  9. customthe main peak collected
  10. customtriturated with DCM

出典と根拠

ORDレコード
ord-73120f5490a84bceb8cc60078f1a266f
出典データセット
uspto-grants-2016_04
特許番号
US09320739B2

関連ノート

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