2-Chlorobenzylamine → 3-(2-methylsulfanyl-pyrimidin-4-yl)-1-oxo-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-2-carboxylic acid 2-chloro-benzylamide

HRID 1455252Notes

Reaction equation

HRID 1455252 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[N:13]3[CH2:14][CH2:15][CH2:16][N:12]3[C:11](=[O:17])[C:10]=2[C:18]([OH:20])=O)[CH:6]=[CH:5][N:4]=1.[Cl:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24][NH2:25].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C([O-])(O)=O.[Na+]>CN(C=O)C>[Cl:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24][NH:25][C:18]([C:10]1[C:11](=[O:17])[N:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:9]=1[C:7]1[CH:6]=[CH:5][N:4]=[C:3]([S:2][CH3:1])[N:8]=1)=[O:20]

Participants

7

Reactant 5

HCID 666482-ChlorobenzylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574380863-(2-methylsulfanyl-pyrimidin-4-yl)-1-oxo-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-2-carboxylic acid

Product 1

HCID 575317953-(2-methylsulfanyl-pyrimidin-4-yl)-1-oxo-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-2-carboxylic acid 2-chloro-benzylamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(2-methylsulfanyl-pyrimidin-4-yl)-1-oxo-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-2-carboxylic acid, 14, (0.23 g, 0.78 mmol) and 2-chlorobenzylamine (0.10 mL, 0.78 mmol) in DMF (3 mL) is added 1-hydroxybenzotriazole (0.21 g, 1.57 mmol) and then 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride (0.18 g, 0.94 mmol). The reaction solution is stirred at room temperature for 6 days then poured into aqueous saturated NaHCO3. The aqueous phase is extracted with three times with EtOAc and the combined organic phases are washed with aqueous saturated NH4Cl, and H2O, dried (MgSO4), filtered and concentrated in vacuo to afford the desired product which is used without further purification: 1H NMR (300 MHz, CDCl3) δ 9.49 (bd s, NH), 8.69 (d, J=5.1 Hz, 1H), 8.16 (d, J=5.1 Hz, 1H), 7.44-7.37 (m, 2H), 7.25-7.19 (m, 2H), 4.70 (d, J=5.4 Hz, 2H), 4.41 (t, J=7.2 Hz, 2H), 4.14 (t, J=7.2 Hz, 2H), 2.78 (dd, J=7.5, 7.5, 7.5, 7.5 Hz, 2H), 2.06 (s, 3H); ESI+ MS: m/z (rel intensity) 415.9 (100, M++H).

Workup

  1. extractionThe aqueous phase is extracted with three times with EtOAc
  2. washthe combined organic phases are washed with aqueous saturated NH4Cl, and H2O
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ab77b3b08c4426790043a9628a995f7
Source dataset
uspto-grants-2009_01
Patent number
US07482356B2

Reaction notes

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