Methanol → HCID 90013599, 화합물

HRID 1051235

반응식

HRID 1051235 반응식
[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]

참가 물질

7

반응물 4

HCID 887MethanolHCID 962WaterHCID 12820921Azane;hydrochlorideHCID 90014153HCID 90014153, 화합물

생성물 1

HCID 90013599HCID 90013599, 화합물수율 48.9%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
70 °C

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-78ad331bab724c7e9e1947e7fda91800
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388170B2

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