Acetic Acid → {2-Amino-6-[2-(tert-butylaminomethyl)-4-fluorophenyl]quinazolin-4-yl}-(1,3-dihydroisoindol-2-yl)methanone

HRID 1631120노트

반응식

HRID 1631120 반응식
[NH2:1][C:2]1[N:11]=[C:10]([C:12]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:23]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:24]=3[CH:25]=O)[CH:8]=2)[N:3]=1.[C:32]([NH2:36])([CH3:35])([CH3:34])[CH3:33].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.O1CCCC1.O>[NH2:1][C:2]1[N:11]=[C:10]([C:12]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:23]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:24]=3[CH2:25][NH:36][C:32]([CH3:35])([CH3:34])[CH3:33])[CH:8]=2)[N:3]=1

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 6385Tert-ButylamineHCID 5049666Sodium triacetoxyborohydrideHCID 871741022-[2-Amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]-5-fluorobenzaldehyde

생성물 1

HCID 56943540{2-Amino-6-[2-(tert-butylaminomethyl)-4-fluorophenyl]quinazolin-4-yl}-(1,3-dihydroisoindol-2-yl)methanone

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

95 mg of 2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]-5-fluorobenzaldehyde are dissolved in 2 ml of 1,2-dichloroethane and 2 ml of tetrahydrofuran. 34 μl of tert-butylamine and 18 μl of glacial acetic acid are added, and the mixture is stirred at 60° C. for 6 h. After cooling to 25° C., 103 mg of sodium triacetoxyborohydride are added and stirred at 25° C. for a further 12 h. The mixture is poured into water, extracted three times with dichloromethane, and the combined organic phases are dried over sodium sulfate. After filtration, the filtrate is evaporated to dryness and purified by chromatography (reversed phase HPLC).

후처리

  1. temperatureAfter cooling to 25° C.
  2. stirringstirred at 25° C. for a further 12 h
  3. extractionextracted three times with dichloromethane
  4. dry with materialthe combined organic phases are dried over sodium sulfate
  5. filtrationAfter filtration
  6. customthe filtrate is evaporated to dryness
  7. custompurified by chromatography (reversed phase HPLC)

출처 및 근거

ORD 기록
ord-331119319e7743f38bfb3d36b18a115f
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791129B2

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