Diisopropylethylamine → HCID 178480483, compound

HRID 874451Notes

Reaction equation

HRID 874451 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][N:5]([CH3:27])[C:6]2[C:7]=1[CH:8]=[CH:9][C:10]1[N:19]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:18][CH:17]=[C:12]3[NH:13][C:14](=[O:16])[C:15]=2[C:11]=13.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:61]1([CH2:67][CH2:68][C:69](O)=[O:70])[CH2:66][CH2:65][CH2:64][CH2:63][CH2:62]1>CN(C)C(=O)C>[F:26][C:23]1[CH:22]=[CH:21][C:20]([N:19]2[C:10]3=[C:11]4[C:15](=[C:6]5[N:5]([CH3:27])[CH:4]=[CH:3][C:2]([NH:1][C:69](=[O:70])[CH2:68][CH2:67][N:61]6[CH2:66][CH2:65][CH2:64][CH2:63][CH2:62]6)=[C:7]5[CH:8]=[CH:9]3)[C:14](=[O:16])[NH:13][C:12]4=[CH:17][CH2:18]2)=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 1177821-Piperidinepropanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178480427HCID 178480427, compound

Product 1

HCID 178480483HCID 178480483, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A stock solution of Example 23e and N,N-diisopropylethylamine (0.165 M and 0.47 M in N,N-dimethylacetamide, respectively, 275 μL, 0.042 mmol Example 23e and 0.13 mmol N,N-diisopropylethylamine), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.25 M in N,N-dimethylacetamide, 253 μL, 0.063 mmol), and 3-(piperidin-1-yl)propanoic acid (0.40 M in N,N-dimethylacetamide, 125 μL, 0.05 mmol) were aspirated from their respective source vials, mixed through a perfluoroalkoxy mixing tube (0.2 mm inner diameter), and loaded into an injection loop. The reaction segment was injected into the flow reactor (Hastelloy coil, 0.75 mm inner diameter, 1.8 mL internal volume) set at 100° C., and passed through the reactor at 180 μL min−1 (10 minute residence time). Upon exiting the reactor, the reaction mixture was loaded directly into an injection loop and purified using reverse phase HPLC(C8, acetonitrile/water (0.1% ammonium acetate), 5-100%) to give 0.0009 g (4%) of the title compound. 1H NMR (400 MHz, DMSO-d6/D2O) δ 8.03 (d, J=2.44 Hz, 1H), 7.56 (s, 1H), 7.38 (dd, J=8.54, 2.44 Hz, 1H), 7.16 (d, J=8.54 Hz, 1H), 6.97 (s, 1H), 6.78 (m, J=8.85, 8.85 Hz, 2H), 6.51 (m, J=9.31, 4.43 Hz, 2H), 4.59 (m, 2H), 4.06 (s, 3H), 2.71 (s, 1H), 2.67 (m, 3H), 2.44 (m, 4H), 1.54 (m, 4H), 1.43 (m, 2H). MS (APCI+) m/z 500.2 (M+H)+.

Workup

  1. additionmixed through a perfluoroalkoxy mixing tube (0.2 mm inner diameter)
  2. customset at 100° C.
  3. custompassed through the reactor at 180 μL min−1 (10 minute residence time)
  4. custompurified

Sources & evidence

ORD record
ord-eaaeaefdba4046fabec4c0672c0a53c8
Source dataset
uspto-grants-2015_03
Patent number
US08980879B2

Reaction notes

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