Diisopropylethylamine → HCID 90114624、化合物

HRID 2275895ノート

反応式

HRID 2275895 の反応式
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[F:34][C:35]1[CH:55]=[CH:54][CH:53]=[C:52]([F:56])[C:36]=1[CH2:37][O:38][C:39]1[C:40]2[N:41]([C:45]([C:49]([OH:51])=O)=[C:46]([CH3:48])[N:47]=2)[CH:42]=[CH:43][CH:44]=1.Cl.Cl.[CH:59]([O:62][CH2:63][CH:64]([NH2:67])[CH2:65][NH2:66])([CH3:61])[CH3:60]>CN(C=O)C.O.C(O)(C(F)(F)F)=O>[NH2:67][CH:64]([CH2:63][O:62][CH:59]([CH3:61])[CH3:60])[CH2:65][NH:66][C:49]([C:45]1[N:41]2[CH:42]=[CH:43][CH:44]=[C:39]([O:38][CH2:37][C:36]3[C:35]([F:34])=[CH:55][CH:54]=[CH:53][C:52]=3[F:56])[C:40]2=[N:47][C:46]=1[CH3:48])=[O:51]

参加物

7

反応物 4

HCID 81531Diisopropylethylamine2 回HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 867178728-((2,6-Difluorobenzyl)oxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acidHCID 90114173HCID 90114173、化合物

生成物 1

HCID 90114624HCID 90114624、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 22392675Trifluoroacetic acid water溶媒

実験手順

125 mg (0.33 mmol) of HATU and 0.16 ml (0.90 mmol) of N,N-diisopropylethylamine were added to 95 mg (0.30 mmol) of 8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid Example 3A in DMF (1.9 ml), and the mixture was stirred at RT for 20 min. At −20° C., 145 mg (0.54 mmol, 76% pure) of rac-3-isopropoxypropane-1,2-diamine dihydrochloride Example 224A in DMF (0.5 ml), to which 0.31 ml (1.8 mmol) of N,N-diisopropylethylamine had been added beforehand and which had been stirred at RT for 10 min, were then slowly added dropwise to the reaction mixture. The mixture was stirred at RT overnight. The mixture was then diluted with water/TFA and purified by prep. RP-HPLC (acetonitrile/water gradient with addition of 0.1% TFA). The product fraction was concentrated and then re-purified by thick-layer chromatography (dichloromethane/methanol: 10:1). This gave 15 mg (12% of theory) of the target compound.

後処理

  1. stirringhad been stirred at RT for 10 min
  2. additionwere then slowly added dropwise to the reaction mixture
  3. stirringThe mixture was stirred at RT overnight
  4. custompurified by prep
  5. additionRP-HPLC (acetonitrile/water gradient with addition of 0.1% TFA)
  6. concentrationThe product fraction was concentrated
  7. customre-purified by thick-layer chromatography (dichloromethane/methanol: 10:1)

出典と根拠

ORDレコード
ord-b58cf17ddf9f407493e15fe3f93092c1
出典データセット
uspto-grants-2015_09
特許番号
US09126998B2

反応ノート

読み込み中…