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Triphenylphosphine → 4-(2,3-dimethylindol-5-ylamino)-6-methoxy-7-((E)-4-(pyrrolidin-1-yl)but-2-en-1-yloxy)quinazoline

HRID 1791639
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HRID 1791639 반응식
N(C(OCC)=O)=NC(OCC)=O.[CH3:13][C:14]1[NH:15][C:16]2[C:21]([C:22]=1[CH3:23])=[CH:20][C:19]([NH:24][C:25]1[C:34]3[C:29](=[CH:30][C:31]([OH:37])=[C:32]([O:35][CH3:36])[CH:33]=3)[N:28]=[CH:27][N:26]=1)=[CH:18][CH:17]=2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:57]1([CH2:62]/[CH:63]=[CH:64]/[CH2:65]O)[CH2:61][CH2:60][CH2:59][CH2:58]1>CN(C=O)C.ClCCl>[CH3:13][C:14]1[NH:15][C:16]2[C:21]([C:22]=1[CH3:23])=[CH:20][C:19]([NH:24][C:25]1[C:34]3[C:29](=[CH:30][C:31]([O:37][CH2:65]/[CH:64]=[CH:63]/[CH2:62][N:57]4[CH2:61][CH2:60][CH2:59][CH2:58]4)=[C:32]([O:35][CH3:36])[CH:33]=3)[N:28]=[CH:27][N:26]=1)=[CH:18][CH:17]=2
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참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22030876(E)-4-(pyrrolidin-1-yl)but-2-en-1-olHCID 1357631094-(2,3-Dimethylindol-5-ylamino)-7-hydroxy-6-methoxyquinazoline

생성물 1

HCID 220309644-(2,3-dimethylindol-5-ylamino)-6-methoxy-7-((E)-4-(pyrrolidin-1-yl)but-2-en-1-yloxy)quinazoline수율 55.7%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

Diethyl azodicarboxylate (65 μl, 0.4 mmol) was added in portions to a suspension of 4-(2,3-dimethylindol-5-ylamino)-7-hydroxy-6-methoxyquinazoline (68 mg, 0.2 mmol), triphenylphosphine (107 mg, 0.4 mmol), (E)-4-(pyrrolidin-1-yl)but-2-en-1-ol (40 mg, 0.28 mmol) in DMF (0.4 ml) and dichloromethane (1.5 ml) cooled at 0° C. The reaction mixture was left to warm up to ambient temperature and was stirred overnight. The mixture was poured onto a column of silica and was eluted with methylene chloride followed by methylene chloride/methanol (98/2), followed by methylene chloride/3N ammonia in methanol (95/5 and 90/10) to give 4-(2,3-dimethylindol-5-ylamino)-6-methoxy-7-((E)-4-(pyrrolidin-1-yl)but-2-en-1-yloxy)quinazoline (51 mg, 55%).

후처리

  1. waitThe reaction mixture was left
  2. temperatureto warm up to ambient temperature
  3. additionThe mixture was poured onto a column of silica
  4. washwas eluted with methylene chloride

출처 및 근거

ORD 기록
ord-2003344db462457e85182b1317dcee08
출처 데이터셋
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07074800B1

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