Methanol → HCID 90013599、化合物

HRID 1051235

反応式

HRID 1051235 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:23][C@H:24]4[CH2:28][CH2:27][O:26][CH2:25]4)=[C:17]([N+:20]([O-])=O)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2].Cl.N.CO.O>[Fe].CC(=O)OCC>[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:23][C@H:24]4[CH2:28][CH2:27][O:26][CH2:25]4)=[C:17]([NH2:20])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2]

参加物

7

反応物 4

HCID 887MethanolHCID 962WaterHCID 12820921Azane;hydrochlorideHCID 90014153HCID 90014153、化合物

生成物 1

HCID 90013599HCID 90013599、化合物収率 48.9%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

(S)—N-(3-ethynylphenyl)-6-nitro-7-(tetrahydrofuran-3-yloxy)quinazolin-4-amine (4 g, 0.011 mol) and ammonia hydrochloride (2.4 g, 0.045 mol) was mixed in a solution of 150 mL methanol, 75 mL H2O, 50 ml EA, and then was heated to 70° C. Fe (4.8 g, 0.085 mol) was added and the reaction mixture was heated to reflux for 4 hours. The resulting reaction solution was filtered and concentrated under reduced pressure to remove most of solvent. The residue was diluted in 100 mL H2O, extracted with ethyl acetate (3×100 mL), the organic layers were concentrated to give (S)—N4-(3-ethynylphenyl)-7-(tetrahydrofuran-3-yloxy)quinazoline-4,6-diamine as grey solid 1.8 g (48.9% yield).

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. customThe resulting reaction solution
  4. filtrationwas filtered
  5. concentrationconcentrated under reduced pressure
  6. customto remove most of solvent
  7. additionThe residue was diluted in 100 mL H2O
  8. extractionextracted with ethyl acetate (3×100 mL)
  9. concentrationthe organic layers were concentrated

出典と根拠

ORDレコード
ord-78ad331bab724c7e9e1947e7fda91800
出典データセット
uspto-grants-2016_07
特許番号
US09388170B2

関連ノート

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