Propylamine → HCID 178457735, compound

HRID 2271100Notes

Reaction equation

HRID 2271100 reaction equation
[O:1]=[C:2]1[C:6]2=[CH:7][NH:8][CH:9]=[C:10]([C:11]([OH:13])=O)[C:5]2=[N:4][N:3]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH2:20]([NH2:23])[CH2:21][CH3:22].O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.C(N(CC)CC)C>CN(C)C(=O)C.O>[CH2:20]([NH:23][C:11]([C:10]1[C:5]2[C:6]([C:2](=[O:1])[N:3]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:4]=2)=[CH:7][NH:8][CH:9]=1)=[O:13])[CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 7852PropylamineHCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 178524797HCID 178524797, compound

Product 1

HCID 178457735HCID 178457735, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 3,5-dihydro-3-oxo-2-phenyl-2H-pyrazolo[4,3-c]pyridine-7-carboxylic acid (50 mg, 0.196 mmol) in anhydrous N,N-dimethylacetamide (2 ml) was added propylamine (17.8 ml, 0.216 mmol), bis(2-oxo-3-oxazolidinyl)phosphinic chloride (55 mg, 0.216 mmol), then, dropwise, anhydrous triethylamine (60 ml, 0.430 mmol). The mixture was stirred under nitrogen at room temperature for 2 h. Water (5 ml) was then added and the mixture was stirred before collecting the solid by filtration. The solid was washed with water, then hexane, and dried under vacuum at 70° C. The solid was then purified by recrystallisation (CH2Cl2-MeOH-EtOAc) to afford 39.1 mg (67%) of the title compound as an orange solid; 1H NMR (360 MHz, DMSO-d6) δ0.99 (3H, t, J 7.3 Hz), 1.62 (2H, sextet, J 7.2 Hz), 3.41 (2H, q, J 6.8 Hz), 7.21 (1H, t, J 7.4 Hz), 7.47 (2H, t, J 7.5 Hz), 8.16 (1H, s), 8.18 (2H, d, J 7.6 Hz), 8.68 (1H, s), 8.70 (1H, t), 12.69 (1H, br s); MS (ES+) m/z 297 [MH]+.

Workup

  1. stirringthe mixture was stirred
  2. custombefore collecting the solid
  3. filtrationby filtration
  4. washThe solid was washed with water
  5. dry with materialhexane, and dried under vacuum at 70° C
  6. customThe solid was then purified by recrystallisation (CH2Cl2-MeOH-EtOAc)

Sources & evidence

ORD record
ord-4c123653c8e747e08ee8e56af32ac555
Source dataset
uspto-grants-2001_12
Patent number
US06333336B1

Reaction notes

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