Triethylamine → Methyl 2-amino-4-(4-methylpiperazin-1-yl)quinazoline-7-carboxylate

HRID 449338노트

반응식

HRID 449338 반응식
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[NH2:8][C:9]1[N:18]=[C:17](Cl)[C:16]2[C:11](=[CH:12][C:13]([C:20]([O:22][CH3:23])=[O:21])=[CH:14][CH:15]=2)[N:10]=1.C(N(CC)CC)C>C(O)C>[NH2:8][C:9]1[N:18]=[C:17]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[C:16]2[C:11](=[CH:12][C:13]([C:20]([O:22][CH3:23])=[O:21])=[CH:14][CH:15]=2)[N:10]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 59496646Methyl 2-amino-4-chloroquinazoline-7-carboxylate

생성물 1

HCID 59496531Methyl 2-amino-4-(4-methylpiperazin-1-yl)quinazoline-7-carboxylate수율 63.1%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
110 °C

실험 절차

1-Methyl-piperazine (210 uL, 1.9 mmol) was added to a mixture of methyl 2-amino-4-chloroquinazoline-7-carboxylate (300 mg, 1 mmol) in ethanol (3 mL) and triethylamine (350 μL, 2.5 mmol). The mixture was heated in an oil bath at 110° C. for 1 h. The reaction mixture was concentrated to remove the ethanol and was partitioned between water and EtOAc. The organic phase was washed with saturated NaCl aqueous solution, dried over MgSO4, filtered, and concentrated to give the crude product, (190 mg, 50%) as an off white amorphous solid. 1H NMR (300 MHz, DMSO) δ 2.23 (s, 3H), 3.56 (m, 4H), 3.86 (s, 3H), 3.90 (m, 4H), 6.53 (b, 2H), 7.50 (d, 1H), 7.80 (m, 2H); Analytic LCMS (M+H)+: m/z=302.1.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customto remove the ethanol
  3. customwas partitioned between water and EtOAc
  4. washThe organic phase was washed with saturated NaCl aqueous solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a21a01cf26c54a7db3f3c61f84f30c47
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481732B2

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