Diisopropylethylamine → HCID 71667528, compound

HRID 1481843Notes

Reaction equation

HRID 1481843 reaction equation
[CH:1]1([C:4]2[O:5][CH:6]=[C:7]([C:9]([OH:11])=O)[N:8]=2)[CH2:3][CH2:2]1.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.[NH2:45][C:46]1[C:47]([N:66]2[CH2:71][CH2:70][N:69]([C:72]3[CH:77]=[CH:76][CH:75]=[CH:74][C:73]=3[CH3:78])[CH2:68][CH2:67]2)=[CH:48][C:49]([O:64][CH3:65])=[C:50]([CH:63]=1)[C:51]([NH:53][CH2:54][CH2:55][CH2:56][N:57]1[CH2:61][CH2:60][CH2:59][C:58]1=[O:62])=[O:52].[Cl-].[Li+]>CN(C=O)C>[CH3:65][O:64][C:49]1[C:50]([C:51](=[O:52])[NH:53][CH2:54][CH2:55][CH2:56][N:57]2[CH2:61][CH2:60][CH2:59][C:58]2=[O:62])=[CH:63][C:46]([NH:45][C:9]([C:7]2[N:8]=[C:4]([CH:1]3[CH2:2][CH2:3]3)[O:5][CH:6]=2)=[O:11])=[C:47]([N:66]2[CH2:67][CH2:68][N:69]([C:72]3[CH:77]=[CH:76][CH:75]=[CH:74][C:73]=3[CH3:78])[CH2:70][CH2:71]2)[CH:48]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 433294Lithium ChlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 252192732-Cyclopropyl-1,3-oxazole-4-carboxylic acidHCID 89690657HCID 89690657, compound

Product 1

HCID 71667528HCID 71667528, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Cyclopropyl-oxazole-4-carboxylic acid 1h (74.8 mg, 0.489 mmol) was taken in DMF (5.0 ml) and HATU (212.3 mg, 0.558 mmol) was added to this and stirred for 3 min. N,N-diisopropylethylamine (0.243 mL, 1.396 mmol) was added to this and the mixture was stirred again for 3 min. 5-Amino-2-methoxy-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-4-(4-o-tolyl-piperazin-1-yl)-benzamide 2b (130.0 mg, 0.279 mmol) was added and the reaction mixture was stirred at room temperature for 16 h. A saturated solution of lithium chloride was added and the product was extracted with ethyl acetate. Organic layer was washed with brine and dried over anhydrous sodium sulfate and concentrated to give the crude product 2c which was purified on preparative HPLC using water/methanol as eluent.

Workup

  1. stirringwas stirred again for 3 min
  2. stirringthe reaction mixture was stirred at room temperature for 16 h
  3. extractionthe product was extracted with ethyl acetate
  4. washOrganic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-93dee837803b48b1bb1035705e93e65e
Source dataset
uspto-grants-2016_08
Patent number
US09409897B2

Reaction notes

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