Piperidine → HCID 11440631, compound

HRID 2242893Notes

Reaction equation

HRID 2242893 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([N:17]=[C:18]([C:20]3[O:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)[CH:5]=[C:6]([C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=2)[C:11]([OH:13])=O)[N:7]=1.CN(C(ON1N=N[C:35]2[CH:36]=[CH:37][CH:38]=[N:39][C:34]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1CCCCC1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[NH2:1][C:2]1[C:3]2[N:4]([N:17]=[C:18]([C:20]3[O:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)[CH:5]=[C:6]([C:8]2[CH:9]=[C:10]([C:11]([N:39]3[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]3)=[O:13])[CH:14]=[CH:15][CH:16]=2)[N:7]=1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11278675HCID 11278675, compound

Product 1

HCID 11440631HCID 11440631, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(8-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-benzoic acid (20.mg, 0.063 mmol; see Example 5 above), HATU (30 mg, 0.095 mmol), piperdine (0.125 mmol), and diisopropylethylamine (11 μL, 0.063 mmol) in DMF (200 μL) was stirred at room temperature for 30 minutes. The solvent was removed, and the residue was purified by HPLC (C18, H2O:MeCN gradient) to afford the product as a white solid (15 mg, 62%). 1H NMR (300 MHz, DMSO-d6) δ 1.56 (br. s, 6H),3.35 (br. s,2H), 3.65 (br. s, 2H), 6.76 (dd, J=3.4, 1.7 Hz, 1H), 7.18 (dd, J=3.4, 0.8 Hz, 1H), 7.4 (br. dt, J=7.6, 1.4 Hz, 1H), 7.56 (t, J=7.6 Hz, 1H), 7.63 (br. s, 2H), 7.96 (dd, J=1.7, 0.8 Hz, 1H), 8.11 (br. s, 1H), 8.14 (dt, J=7.5, 1.5 Hz, 1H),8.9 (s, 1H).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by HPLC (C18, H2O:MeCN gradient)

Sources & evidence

ORD record
ord-4a8b183324e84b38b48aa17558952a05
Source dataset
uspto-grants-2010_03
Patent number
US07674791B2

Reaction notes

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