Diethylamine → HCID 11426556, compound

HRID 2242896Notes

Reaction equation

HRID 2242896 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([N:11]=[C:12]([C:14]3[O:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:5]=[C:6]([C:8]([OH:10])=O)[N:7]=1.[CH:19]([N:22](C(C)C)[CH2:23][CH3:24])(C)[CH3:20].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(NCC)C>CN(C=O)C>[CH2:19]([N:22]([CH2:23][CH3:24])[C:8]([C:6]1[N:7]=[C:2]([NH2:1])[C:3]2[N:4]([N:11]=[C:12]([C:14]3[O:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:5]=1)=[O:10])[CH3:20]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11402309HCID 11402309, compound

Product 1

HCID 11426556HCID 11426556, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 8-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazine-6-carboxylic acid (20 mg, 0.082 mmol; see Example 8 above), diisopropylethylamine (14 μL, 0.082 mmol), HATU (47 mg, 0.123 mmol), and diethylamine (0.163 mmol) in DMF (300 μL) was stirred at room temperature for 1 hour. The solvent was removed in vacuo. The residue was purified by HPLC (C18, H2O:MeCN gradient). 1H NMR (300 MHz, DMSO-d6) δ 1.17 (t, J=6.9 Hz, 6H), 3.41 (m, 4H), 6:76 (dd, J3.4, 1.7 Hz, 1H), 7.18 (dd, J=3.4, 0.7 Hz, 1H), 7.69 (br. s, 2H), 7.96 (dd, J=1.7, 0.7 Hz), 8.34 (s, 1H). MS: m/z 301 (M+1).

Workup

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

Sources & evidence

ORD record
ord-4f424497dced4345948f008e1c1079c5
Source dataset
uspto-grants-2010_03
Patent number
US07674791B2

Reaction notes

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