Triethylamine → HCID 178433632, compound

HRID 2271107Notes

Reaction equation

HRID 2271107 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:26](=[O:27])[C:11]3=[CH:12][NH:13][C:14]([CH3:25])=[C:15]([C:16]4[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=4)[C:19](O)=[O:20])[C:10]3=[N:9]2)=[CH:4][CH:3]=1.[NH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.C(N(CC)CC)C>CN(C)C(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:26](=[O:27])[C:11]3=[CH:12][NH:13][C:14]([CH3:25])=[C:15]([C:16]4[CH:24]=[CH:23][CH:22]=[C:18]([C:19]([N:28]5[CH2:32][CH2:31][CH2:30][CH2:29]5)=[O:20])[CH:17]=4)[C:10]3=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 178433633HCID 178433633, compound

Product 1

HCID 178433632HCID 178433632, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 3-[2-(4-chlorophenyl)-3,5-dihydro-6-methyl-3-oxo-2H-pyrazolo[4,3-c]pyridin-7-yl]benzoic acid (65 mg, 0.171 mmol) in anhydrous N,N-dimethylacetamide (2 ml) was added pyrrolidine (15.7 ml, 0.188 mmol), bis(2-oxo-3-oxazolidinyl)phosphinic chloride (48.0 mg, 0.188 mmol), then, dropwise, anhydrous triethylamine (52.5 ml, 0.376 mmol). The mixture was stirred under nitrogen at room temperature for 18 h. The solvent was removed in vacuo and the residue was purified by flash chromatography (silica gel, 3-5% MeOH/CH2Cl2) to give 63.2 mg (85%) of the title compound as a yellow solid; mp 253-255° C.; 1H NMR (360 MHz, DMSO-d6) δ1.85 (4H, m), 2.29 (3H, s), 3.49 (4H, br q, J 6.9 Hz), 7.41 (2H, d, J 9.0 Hz), 7.55-7.59 (3H, m), 7.66 (1H, s), 8.12 (2H, d, J 9.0 Hz), 8.58 (1H, s), 12.49 (1H, br s); MS (ES+) m/z 433/435 [H]+. Anal. found: C, 63.85; H, 4.96; N, 12.33. C24H21ClN4O2.H2O requires: C, 63.93; H, 5.14; N, 12.42%.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash chromatography (silica gel, 3-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-a2e7f9e5895d4dddb02030e8bc2433af
Source dataset
uspto-grants-2001_12
Patent number
US06333336B1

Reaction notes

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