Diisopropylethylamine → HCID 89692815, compound

HRID 1481846Notes

Reaction equation

HRID 1481846 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([C:33]([F:36])([F:35])[F:34])[C:19]=1[N:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:32])[CH2:22][CH2:21]1)[C:5]([NH:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:15][CH2:14][CH2:13][C:12]1=[O:16])=[O:6].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.[CH:70]1([C:73]2[O:74][CH:75]=[C:76]([C:78](O)=[O:79])[N:77]=2)[CH2:72][CH2:71]1.[Cl-].[Li+]>CN(C=O)C>[O:16]=[C:12]1[CH2:13][CH2:14][CH2:15][N:11]1[CH2:10][CH2:9][CH2:8][NH:7][C:5]([C:4]1[CH:17]=[C:18]([C:33]([F:36])([F:35])[F:34])[C:19]([N:20]2[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])[CH2:22][CH2:21]2)=[C:2]([NH:1][C:78]([C:76]2[N:77]=[C:73]([CH:70]3[CH2:72][CH2:71]3)[O:74][CH:75]=2)=[O:79])[CH:3]=1)=[O:6]

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 89691454HCID 89691454, compound

Product 1

HCID 89692815HCID 89692815, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-amino-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-4-(4-o-tolyl-piperazin-1-yl)-5-trifluoromethyl-benzamide 4d (87.0 mg, 0.173 mmol) in DMF (3.0 mL) was added HATU (131.4 mg, 0.346 mmol) and stirred for 4 min. N,N-diisopropylethylamine (0.11 g, 0.86 mmol) was added to this and the solution was stirred for another 4 min. 2-Cyclopropyl-oxazole-4-carboxylic acid 1h (39.6 mg, 0.26 mmol) was added to this and the reaction was stirred at 25° C. for 16 h. A saturated solution of lithium chloride was added and extracted with ethyl acetate. Organic layer was washed with brine and dried on anhydrous sodium sulfate, concentrated and the crude 4e was dissolved in methanol and purified on preparative HPLC using water/methanol as eluent.

Workup

  1. stirringwas stirred for another 4 min
  2. stirringwas stirred at 25° C. for 16 h
  3. extractionextracted with ethyl acetate
  4. washOrganic layer was washed with brine
  5. dry with materialdried on anhydrous sodium sulfate
  6. concentrationconcentrated
  7. dissolutionthe crude 4e was dissolved in methanol
  8. custompurified on preparative HPLC

Sources & evidence

ORD record
ord-459d6fc9c8c6467a9cb76e08d0072204
Source dataset
uspto-grants-2016_08
Patent number
US09409897B2

Reaction notes

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