Triethylamine → HCID 71699909, compound

HRID 456125Notes

Reaction equation

HRID 456125 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[C:16]4=[N:17][C:18]([C:21](=O)[CH3:22])=[CH:19][N:20]=[C:15]4[N:14]=[N:13]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.[NH:25]([C:27]([NH2:29])=[O:28])[NH2:26].C(N(CC)CC)C>CO>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[C:16]4=[N:17][C:18](/[C:21](=[N:26]/[NH:25][C:27]([NH2:29])=[O:28])/[CH3:22])=[CH:19][N:20]=[C:15]4[N:14]=[N:13]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11236Semicarbazide hydrochlorideHCID 593418021-(1-(Quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone

Product 1

HCID 71699909HCID 71699909, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
37 °C

Procedure

To a solution of 1-(1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone (35 mg, 0.115 mmol) in MeOH (3 mL), was added hydrazinecarboxamide hydrochloride (115 mg, 1.035 mmol). The solution was heated to 37° C. overnight. Triethyl amine (1 mL) was added and the solution was stirred at rt for 20 min. Solvents were removed in vacuo and the residue was diluted with DCM, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to afford 25 mg of the title compound in 57% yield as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.90 (s, 1H), 9.85 (s, 1H), 8.89 (m, 1H), 3.36 (d, 1H), 8.01 (m, 2H), 7.82 (d, 1H), 7.53 (dd, 1H), 6.17 (s, 2H), 2.32 (s, 3H). LCMS (method A): [MH]+=384, tR=4.09 min.

Workup

  1. customSolvents were removed in vacuo
  2. additionthe residue was diluted with DCM
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e760de9e5d124445a5619721fb714e70
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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