HCID 56646749, compound → 3-(4-Oxo-6-(pyrrolidin-1-yl)-1,4-dihydroquinolin-2-yl)phenyl dihydrogen phosphate

HRID 38644Notes

Reaction equation

HRID 38644 reaction equation
[P:1]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]2[NH:27][C:28]3[C:33]([C:34](=[O:36])[CH:35]=2)=[CH:32][C:31]([N:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)=[CH:30][CH:29]=3)[CH:21]=1)([O:11]CC1C=CC=CC=1)([O:3]CC1C=CC=CC=1)=[O:2]>CO.[Pd]>[P:1]([OH:11])([OH:3])([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]2[NH:27][C:28]3[C:33]([C:34](=[O:36])[CH:35]=2)=[CH:32][C:31]([N:37]2[CH2:38][CH2:39][CH2:40][CH2:41]2)=[CH:30][CH:29]=3)[CH:21]=1)=[O:2]

Participants

4

Reactant 1

HCID 56646749HCID 56646749, compound

Product 1

HCID 566455293-(4-Oxo-6-(pyrrolidin-1-yl)-1,4-dihydroquinolin-2-yl)phenyl dihydrogen phosphateYield 69.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 146 (200 mg, 0.36 mmol) in anhydrous MeOH (10 mL) was hydrogenated in the presence of 10% Pd/C (100 mg) at 25° C. for 20 min. The catalyst and precipitate were collected and dissolved in 10% NaHCO3 solution and then filtered. The filtrate was acidified with dil aq HCl and the precipitate was then collected and washed with acetone to give 147 (97 mg, 0.25 mmol). Yellow solid; yield: 69.8%; mp>300° C.; MS (ESI): m/z 387.1 (M+H)+; 1H-NMR (D2O+NaOD, 200 MHz): δ 1.78 (m, 4H), 3.08 (m, 4H), 6.70 (s, 1H), 7.12-7.20 (m, 3H), 7.28 (t, J=7.8 Hz, 1H), 7.40 (d, J=7.6 Hz, 1H), 7.49 (s, 1H), 7.61 (d, J=9.8 Hz, 1H); Anal. (C19H19N2O5P) C, H, N.

Workup

  1. customThe catalyst and precipitate were collected
  2. dissolutiondissolved in 10% NaHCO3 solution
  3. filtrationfiltered
  4. customthe precipitate was then collected
  5. washwashed with acetone

Sources & evidence

ORD record
ord-de5a9b01489e43b2b832db492cc5cd89
Source dataset
uspto-grants-2013_09
Patent number
US08524740B2

Reaction notes

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