Triphenylphosphine → 4-Chloro-6-methoxy-7-[3-(4-prop-2-yn-1-ylpiperazin-1-yl)propoxy]quinazoline

HRID 2068125노트

반응식

HRID 2068125 반응식
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:14])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:34]([N:37]1[CH2:42][CH2:41][N:40]([CH2:43][CH2:44][CH2:45]O)[CH2:39][CH2:38]1)[C:35]#[CH:36]>ClCCl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:45][CH2:44][CH2:43][N:40]3[CH2:39][CH2:38][N:37]([CH2:34][C:35]#[CH:36])[CH2:42][CH2:41]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 450998243-(4-Prop-2-YN-1-ylpiperazin-1-YL)propan-1-OLHCID 1357422514-Chloro-6-methoxyquinazolin-7-ol

생성물 1

HCID 589602354-Chloro-6-methoxy-7-[3-(4-prop-2-yn-1-ylpiperazin-1-yl)propoxy]quinazoline수율 77%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

4-Chloro-7-hydroxy-6-methoxyquinazoline (300 mg, 1.42 mmol), (prepared as described for the starting material in Example 4), was suspended in dichloromethane (15 ml). Triphenylphosphine (523 mg, 2 mmol) and 3-(4-prop-2-yn-1-ylpiperazin-1-yl)propan-1-ol (267 mg, 1.46 mmol) were added. Diisopropyl azadicarboxylate (340 μl, 1.71 mmol) was then added dropwise. The reaction mixture was stirred for 1.25 hours at ambient temperature and then loaded directly onto a silica column, and eluted with methylene chloride/methanol (90/8 followed by 90/10) to give 4-chloro-6-methoxy-7-[3-(4-prop-2-yn-1-ylpiperazin-1-yl)propoxy]quinazoline (409 mg, 77%).

후처리

  1. additionDiisopropyl azadicarboxylate (340 μl, 1.71 mmol) was then added dropwise
  2. washeluted with methylene chloride/methanol (90/8 followed by 90/10)

출처 및 근거

ORD 기록
ord-4ac9bb9ccf034c2d9476593e58eafda8
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293902B2

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