2-Hydroxy-gamma-butyrolactone, (2S)- → (2S)-N-{2-[(4-{[3-Chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}-2,4-dihydroxybutanamide

HRID 1864272노트

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HRID 1864272 반응식
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[C:7]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[C:18]([Cl:30])[CH:17]=1)=[N:8][CH:9]=[N:10]2.[OH:31][C@H:32]1[CH2:37][CH2:36][O:35][C:33]1=[O:34]>C1(C)C(C)=CC=CC=1>[Cl:30][C:18]1[CH:17]=[C:16]([NH:15][C:7]2[C:6]3[C:11](=[CH:12][CH:13]=[CH:14][C:5]=3[O:4][CH2:3][CH2:2][NH:1][C:33](=[O:34])[C@@H:32]([OH:31])[CH2:37][CH2:36][OH:35])[N:10]=[CH:9][N:8]=2)[CH:21]=[CH:20][C:19]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1

참가 물질

4

반응물 2

HCID 3578532-Hydroxy-gamma-butyrolactone, (2S)-2회HCID 69057714HCID 69057714, 화합물

생성물 1

HCID 57974330(2S)-N-{2-[(4-{[3-Chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}-2,4-dihydroxybutanamide수율 69%

시약·촉매·용매 1

HCID 7237O-Xylene용매

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온도
130 °C

실험 절차

5-(2-aminoethoxy)-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]quinazolin-4-amine (obtained as described in Example 2.6, preparation of starting materials, 0.5 g, 1.19 mmol) was heated to 130° C. in xylene (20 ml) until it had dissolved. (S)-(−)-α-hydroxy-γ-butyrolactone (0.10 ml, 1.31 mmol) was added and the mixture was stirred at 130° C. for 3 hours. More (S)-(−)-α-hydroxy-γ-butyrolactone (0.05 ml, 0.66 mmol) was added and the mixture was heated for a further 2 hours. The resultant precipitate was filtered off while the mixture was hot, washed with diethyl ether (3×10 ml) and dried to give the title compound as a solid (430 mg, 69%); NMR spectrum (DMSO-d6) 1.38-1.55 (m, 1H), 1.69-1.85 (m, 1H), 3.37-3.50 (m, 2H), 3.61-3.77 (m, 2H), 3.89-4.00 (m, 1H), 4.28-4.45 (m, 3H), 5.29 (s, 2H), 5.51 (d, 1H), 7.13 (d, 1H), 7.22 (d, 1H), 7.28-7.41 (m, 2H), 7.49-7.62 (m, 2H), 7.71 (t, 1H), 8.01 (d, 1H), 8.14-8.25 (m, 1H), 8.45 (s, 1H), 8.59 (d, 1H), 9.82 (s, 1H); Mass spectrum MH+ 523.9.

후처리

  1. dissolutionhad dissolved
  2. temperaturethe mixture was heated for a further 2 hours
  3. filtrationThe resultant precipitate was filtered off while the mixture
  4. washwashed with diethyl ether (3×10 ml)
  5. customdried

출처 및 근거

ORD 기록
ord-7ded10027d8a462c88132ff22456e8de
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07625908B2

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