Diisopropylethylamine → HCID 47017927, compound

HRID 2402331Notes

Reaction equation

HRID 2402331 reaction equation
[NH2:1][C:2]1[O:3][C:4]([C:7]2[O:8][CH:9]=[CH:10][CH:11]=2)=[N:5][N:6]=1.C1C=NC2N(O)N=NC=2C=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.[C:55]1([C:61]2[N:66]=[C:65]3[N:67]=[C:68]([N:70]4[CH2:75][CH2:74][CH2:73][CH2:72][CH2:71]4)[S:69][C:64]3=[C:63]([C:76](O)=[O:77])[CH:62]=2)[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1>CN(C=O)C.O>[O:8]1[CH:9]=[CH:10][CH:11]=[C:7]1[C:4]1[O:3][C:2]([NH:1][C:76]([C:63]2[CH:62]=[C:61]([C:55]3[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=3)[N:66]=[C:65]3[N:67]=[C:68]([N:70]4[CH2:75][CH2:74][CH2:73][CH2:72][CH2:71]4)[S:69][C:64]=23)=[O:77])=[N:6][N:5]=1

Participants

8

Reactant 5

HCID 81531Diisopropylethylamine2×HCID 181649HOAt2×HCID 2021855-(Furan-2-yl)-1,3,4-oxadiazol-2-amine2×HCID 2560413852388-80-8HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×

Product 1

HCID 47017927HCID 47017927, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Amino-5-(2-furyl)-1,3,4-oxadiazole (76 mg, 0.50 mmol), HOAt (68 mg, 0.50 mmol), HATU (190 mg, 0.50 mmol), and N,N-diisopropylethylamine (97 μL, 0.56 mmol) were added to a solution of commercially available 5-phenyl-2-piperidino-7-thiazolo[4,5-b]pyridinecarboxylic acid (85 mg, 0.25 mmol) in DMF (1 mL), followed by stirring overnight at room temperature in an argon atmosphere. To the reaction solution were added 2-amino-5-(2-furyl)-1,3,4-oxadiazole (76 mg, 0.50 mmol), HOAt (68 mg, 0.50 mmol), HATU (190 mg, 0.50 mmol), and N,N-diisopropylethylamine (97 μL, 0.56 mmol), and the mixture was stirred at room temperature for further 4 days. Water was added to the reaction solution, and the precipitated crystals were collected by filtration, washed with water, and recrystallized from methanol to obtain the title compound (27 mg, 0.06 mmol) (yield: 240).

Workup

  1. stirringthe mixture was stirred at room temperature for further 4 days
  2. filtrationthe precipitated crystals were collected by filtration
  3. washwashed with water
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-50154004bfb748c5905f3c673fa94578
Source dataset
uspto-grants-2014_08
Patent number
US08796320B2

Reaction notes

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