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Red-Al → (3-{4-[3-Chloro-4-(3-fluoro-benzyloxy)-phenylamino]-quinazolin-6-yl}-allyl)-carbamic acid tert-butyl ester

HRID 503707
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HRID 503707 반응식
[C:1]([O:5][C:6](=[O:38])[NH:7][CH2:8][C:9]#[C:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][N:15]=[C:14]2[NH:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=2)=[C:24]([Cl:37])[CH:23]=1)([CH3:4])([CH3:3])[CH3:2].COCCO[AlH2-]OCCOC.[Na+]>C1(C)C=CC=CC=1.C1COCC1>[C:1]([O:5][C:6](=[O:38])[NH:7][CH2:8][CH:9]=[CH:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][N:15]=[C:14]2[NH:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=2)=[C:24]([Cl:37])[CH:23]=1)([CH3:4])([CH3:2])[CH3:3]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 16684438Red-AlHCID 66623753(3-{4-[3-Chloro-4-(3-fluoro-benzyloxy)-phenylamino]-quinazolin-6-yl}-prop-2-ynyl)-carbamic acid tert-butyl ester

생성물 1

HCID 68463615(3-{4-[3-Chloro-4-(3-fluoro-benzyloxy)-phenylamino]-quinazolin-6-yl}-allyl)-carbamic acid tert-butyl ester

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran
용매

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온도
0 °C

실험 절차

(3-{4-[3-Chloro-4-(3-fluoro-benzyloxy)-phenylamino]-quinazolin-6-yl}-allyl)-carbamic acid tert-butyl ester is prepared by adding (3-{4-[3-chloro-4-(3-fluoro-benzyloxy)-phenylamino]-quinazolin-6-yl}-prop-2-ynyl)-carbamic acid tert-butyl ester (3.00 g, 5.63 mmol) to a mixture of Red-Al (5 ml of a 65% wt solution in toluene) in THF (50 ml) at 0° C. under N2. After stirring for 3 h at 0° C., the reaction mixture is quenched by the addition of 10 ml of 10% K2CO3 solution followed by water. The reaction mixture is extracted with ethyl acetate. The organic extracts are dried (Na2SO4), concentrated, and purified by column chromatography (EtOAc:Hex 1:1) to provide 2.01 g (67%) clean desired product.

후처리

  1. customthe reaction mixture is quenched by the addition of 10 ml of 10% K2CO3 solution
  2. extractionThe reaction mixture is extracted with ethyl acetate
  3. dry with materialThe organic extracts are dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified by column chromatography (EtOAc:Hex 1:1)

출처 및 근거

ORD 기록
ord-d45001185b834960b90ad08929dea25f
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07777032B2

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