Diisopropylethylamine → HCID 90114624, 화합물

HRID 2275895노트

반응식

HRID 2275895 반응식
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]

참가 물질

7

반응물 4

HCID 81531Diisopropylethylamine2회HCID 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, 화합물

생성물 1

HCID 90114624HCID 90114624, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 22392675Trifluoroacetic acid water용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b58cf17ddf9f407493e15fe3f93092c1
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126998B2

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