Sodium Bicarbonate → tert-butyl ((3R,4S)-4-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)tetrahydrofuran-3-yl)carbamate

HRID 56368

반응식

HRID 56368 반응식
Cl[C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]3[C:17]([Cl:18])=[C:16]([O:19][CH3:20])[CH:15]=[C:14]([O:21][CH3:22])[C:13]=3[Cl:23])[CH:8]=2)[N:3]=1.[NH2:24][C@@H:25]1[CH2:29][O:28][CH2:27][C@@H:26]1[NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34].C(=O)(O)[O-].[Na+]>CN1C(=O)CCC1>[Cl:18][C:17]1[C:16]([O:19][CH3:20])=[CH:15][C:14]([O:21][CH3:22])=[C:13]([Cl:23])[C:12]=1[C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH:24][C@@H:25]1[CH2:29][O:28][CH2:27][C@@H:26]1[NH:30][C:31](=[O:37])[O:32][C:33]([CH3:35])([CH3:34])[CH3:36])[N:11]=[CH:10]2

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 899217722-Chloro-6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolineHCID 90436776tert-butyl ((3R,4S)-4-aminotetrahydrofuran-3-yl)carbamate

생성물 1

HCID 118043440tert-butyl ((3R,4S)-4-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)tetrahydrofuran-3-yl)carbamate수율 74.5%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

A mixture of 2-chloro-6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazoline (1.02 g, 2.76 mmol), tert-butyl ((3R,4S)-4-aminotetrahydrofuran-3-yl)carbamate (0.85 g, 4.20 mmol), and sodium bicarbonate (0.58 g, 6.90 mmol) was stirred in NMP (5.5 mL, 0.5M) at 95° C. for 12 hours. The reaction was removed from the oil bath and while cooling to room temperature was treated with about 90 mL of water and then sonicated and stirred for 20 minutes. A yellow-orange solid was isolated by filtration, rinsed several times with small amounts of water, and dried under vacuum for nearly 1 hour to yield 3.35 g of crude, which was purified by silica gel chromatography to yield 1.10 g (74.5% yield) of tert-butyl ((3R,4S)-4-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)tetrahydrofuran-3-yl)carbamate as a light yellow foam. MS (ES+) C25H28Cl2N4O5 requires: 534, found: 535 [M+H]+.

후처리

  1. customThe reaction was removed from the oil bath
  2. additionwas treated with about 90 mL of water
  3. customsonicated
  4. customA yellow-orange solid was isolated by filtration
  5. washrinsed several times with small amounts of water
  6. customdried under vacuum for nearly 1 hour
  7. customto yield 3.35 g of crude, which
  8. customwas purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-dd24e3903a2548b6a8085bfc0b373487
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434700B2

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