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Dibutyltin oxide → {5-[2-[(N-Benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-(2H-tetrazol-5-yl)-phenyl]-pyridin-3-yl}-acetic acid

HRID 554594
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HRID 554594 반응식
[CH2:1]([O:3][C:4](=[O:34])[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][C:13]=2[CH2:20][N:21]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]([CH:24]2[CH2:26][CH2:25]2)=[O:23])[CH:11]=1)[CH3:2].C([Sn](=O)CCCC)CCC.[N:45]([Si](C)(C)C)=[N+:46]=[N-:47]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:34])[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:45]=[N:46][NH:47][N:19]=3)=[CH:14][C:13]=2[CH2:20][N:21]([CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:22]([CH:24]2[CH2:26][CH2:25]2)=[O:23])[CH:11]=1)[CH3:2].[CH2:27]([N:21]([CH2:20][C:13]1[CH:14]=[C:15]([C:18]2[N:45]=[N:46][NH:47][N:19]=2)[CH:16]=[CH:17][C:12]=1[C:10]1[CH:11]=[C:6]([CH2:5][C:4]([OH:3])=[O:34])[CH:7]=[N:8][CH:9]=1)[C:22]([CH:24]1[CH2:25][CH2:26]1)=[O:23])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 67212964(5-{2-[(Benzyl-cyclopropanecarbonyl-amino)-methyl]-4-cyano-phenyl}-pyridin-3-yl)-acetic acid ethyl ester

생성물 2

HCID 45138332{5-[2-[(N-Benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-(2H-tetrazol-5-yl)-phenyl]-pyridin-3-yl}-acetic acid
HCID 58565080
{5-[2-[(N-benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-(2H-tetrazol-5-yl)-phenyl]-pyridin-3-yl}-acetic acid ethyl ester

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
80 °C

실험 절차

(5-{2-[(N-Benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-cyano-phenyl}-pyridin-3-yl)-acetic acid ethyl ester (0.253 g, 0.56 mmol) was dissolved in toluene (10 mL). Dibutyltin oxide (0.014 g, 0.06 mmol) was added, followed by azidotrimethylsilane (0.09 mL, 0.67 mmol), and the reaction was stirred at 80° C. for 5 hours, and at 100° C. overnight. The mixture was quenched with H2O and extracted with EtOAc. The combined organic layers were concentrated and purified by preparative HPLC to give {5-[2-[(N-benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-(2H-tetrazol-5-yl)-phenyl]-pyridin-3-yl}-acetic acid ethyl ester the title compound.

후처리

  1. customat 100° C.
  2. customovernight
  3. customThe mixture was quenched with H2O
  4. extractionextracted with EtOAc
  5. concentrationThe combined organic layers were concentrated
  6. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-1905ee7ed9154e29b9343731b18b9e54
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08049015B2

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