Dimethylamine → HCID 11500629, compound

HRID 1430343Notes

Reaction equation

HRID 1430343 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[NH:10][C:9]([C:16]([OH:18])=[O:17])=[CH:8]2.[NH:19]([CH3:21])[CH3:20].C([O-])([O-])=O.[Na+].[Na+]>O>[ClH:1].[CH3:20][N:19]([CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[NH:10][C:9]([C:16]([OH:18])=[O:17])=[CH:8]2)[CH3:21]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 10340Sodium CarbonateHCID 11514561HCID 11514561, compound

Product 1

HCID 11500629HCID 11500629, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

A mixture of acid 18 (300 mg, 1.11 mmol), 40% aqueous Me2NH (2.81 mL, 22.2 mmol), Na2CO3 (295 mg, 2.78 mmol), and water (20 mL) was stirred at 100° C. for 1.5 h. After cooling to room temperature the solvent was removed in vacuo, the residue was dissolved in water (15 mL), and the resulting solution was acidified with 2 M HCl. Then, the solution was evaporated to dryness and the resulting crude product was purified by column chromatography on silica gel (MeOH/CH2Cl2, 10:1, 1% conc. HCl) to provide a green solid which was dissolved in water. Insoluble silica gel was removed by filtration, the water was removed under reduced pressure and the residue was dried in vacuo to give 19 (343 mg, 98%) as a grey-green solid. 1H NMR (300 MHz, DMSO-d6): δ=2.87 (s, 6 H, NMe2), 3.49 (t, J=5.0 Hz, 2 H, 2′-H2), 3.82 (s, 3 H, OMe), 4.34 (t, J=5.0 Hz, 2 H, 1′-H2), 6.94 (s, 1 H, 7-H), 6.97 (d, J=1.8 Hz, 1 H, 3-H), 7.23 (s, 1 H, 4-H), 10.99 (sbr, 1 H, NH+), 11.50 (sbr, 1 H, NH), 12.60 (sbr, 1 H, CO2H) ppm; 13C NMR (50.3 MHz, DMSO-d6): δ=42.7 (NMe2), 55.2 (C-2′), 55.6 (OMe), 64.5 (C-1′), 94.8 (C-7), 106.2 (C-4), 107.5 (C-3), 119.7 (C-3a), 127.0 (C-2), 133.2 (C-7a), 143.4 (C-5), 149.4 (C-6), 162.4 (C═O) ppm; MS (70 eV, EI): m/z (%)=278 (7) [M−HCl]+, 58 (100) [CH2NMe2]+; C14H19ClN2O4 (314.76): calcd. 278.1267 [M−HCl]+, found 278.1267.

Workup

  1. temperatureAfter cooling to room temperature the solvent
  2. customwas removed in vacuo
  3. dissolutionthe residue was dissolved in water (15 mL)
  4. customThen, the solution was evaporated to dryness
  5. customthe resulting crude product was purified by column chromatography on silica gel (MeOH/CH2Cl2, 10:1, 1% conc. HCl)
  6. customto provide a green solid which
  7. customInsoluble silica gel was removed by filtration
  8. customthe water was removed under reduced pressure
  9. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-9b2b552ac75449b7af8ccdb9d1a42a82
Source dataset
uspto-grants-2015_01
Patent number
US08940784B2

Reaction notes

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