Hydrochloric Acid → HCID 59393652, compound

HRID 2092138Notes

Reaction equation

HRID 2092138 reaction equation
Cl.C([O:6][C:7]([C:9]1[N:10]=[N:11][C:12]([C:15]2[CH:16]=[N:17][C:18]([C:21]([C:26]3[CH:31]=[CH:30][C:29]([C:32]4[CH:33]=[N:34][C:35]([N:38]5[C:42]([CH3:43])=[CH:41][CH:40]=[C:39]5[CH3:44])=[N:36][CH:37]=4)=[CH:28][CH:27]=3)([CH3:25])[CH:22]([CH3:24])[CH3:23])=[CH:19][CH:20]=2)=[CH:13][CH:14]=1)=[CH2:8])CCC.C(=O)(O)[O-].[Na+].[Cl-].[Na+]>CCO>[CH3:44][C:39]1[N:38]([C:35]2[N:34]=[CH:33][C:32]([C:29]3[CH:28]=[CH:27][C:26]([C:21]([C:18]4[N:17]=[CH:16][C:15]([C:12]5[N:11]=[N:10][C:9]([C:7](=[O:6])[CH3:8])=[CH:14][CH:13]=5)=[CH:20][CH:19]=4)([CH3:25])[CH:22]([CH3:23])[CH3:24])=[CH:31][CH:30]=3)=[CH:37][N:36]=2)[C:42]([CH3:43])=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid4×HCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 59393677HCID 59393677, compound

Product 1

HCID 59393652HCID 59393652, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

Hydrochloric acid (100 mL of a 1.0 M solution in EtOH) was added to a stirred solution of 4y (7.03 g, 12.3 mmol) in EtOH (50.0 mL) at 0° C. After approximately 15 min, a second portion of hydrochloric acid (100 mL of a 2.0 M aqueous solution) was added, and after another 15 min, a third portion of hydrochloric acid (100 mL of a 1.0 M solution in EtOH). After an additional 15 min, a final portion of hydrochloric acid (50 mL of a 6.0 M aqueous solution) was added, and the resulting reaction was aged for 30 min. The reaction was carefully neutralized by the addition of solid sodium bicarbonate. The resulting mixture was saturated with solid sodium chloride and extracted twice with EtOAc. The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated in vacuo to afford the title compound 4z m/z (ES) 517 (MH)+. 1HNMR (500 MHz, CDCl3): δ 9.32 (d, 1H, J=2.3 Hz), 8.95 (s, 2H), 8.47 (dd, 1H, J=2.3, 8.5 Hz), 8.22 (d, 1H, J=8.9 Hz), 8.04 (d, 1H, J=8.9 Hz), 7.58 (m, 4H), 7.50 (d, 1H, J=8.4 Hz), 5.91 (s, 2H), 3.24 (m, 1H), 2.94 (s, 3H), 2.37 (s, 6H), 1.82 (s, 3H), 0.94 (d, 3H, J=6.6 Hz), 0.89 (d, 3H, J=6.6 Hz).

Workup

  1. waitafter another 15 min
  2. waitAfter an additional 15 min
  3. customthe resulting reaction
  4. waitwas aged for 30 min
  5. extractionextracted twice with EtOAc
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (sodium sulfate)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-33777edbe57c406d818a39a3e516f180
Source dataset
uspto-grants-2013_05
Patent number
US08440672B2

Reaction notes

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