Hydrochloric Acid → HCID 54597140, compound

HRID 2066421Notes

Reaction equation

HRID 2066421 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:26]=[C:25]4[C:21]([C:22]([C:35]5[CH:36]=[N:37][N:38]([CH3:40])[CH:39]=5)=[N:23][N:24]4COCC[Si](C)(C)C)=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:26]=[C:25]4[C:21]([C:22]([C:35]5[CH:36]=[N:37][N:38]([CH3:40])[CH:39]=5)=[N:23][NH:24]4)=[CH:20][CH:19]=3)=[CH:16][CH:17]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66995496HCID 66995496, compound

Product 1

HCID 54597140HCID 54597140, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of Example 1E (45 mg, 0.081 mmol) in ethanol (6 ml) was treated with 2 ml of a 6N HCl solution, refluxed for 1 hour, then cooled and concentrated to near dryness. The residue was triturated with water and the resulting solid was collected, dissolved in methanol and CH2Cl, adsorbed onto Celite, and purified by silica gel chromatography (4% methanol in CH2Cl2) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.94 (s, 3 H) 6.79 (dt, J=8.82 Hz, 2.37 Hz, 1 H) 7.15 (d, J=8.14 Hz, 1 H) 7.32 (q, J=8.14 Hz, 1 H) 7.45 (dd, J=8.48 Hz, 1.36 Hz, 1 H) 7.51 (dt, J=2.37 Hz, 11.87 Hz, 1 H) 7.59 (m, 2 H) 7.69 (m, 3 H) 7.99 (s, 1 H) 8.05 (d, J=8.48 Hz, 1 H) 8.37 (s, 1 H) 8.89 (s, 1 H) 8.96 (s, 1 H) 12.94 (s, 1 H). MS (ESI(+)) m/e 427 (M+H)+.

Workup

  1. temperaturerefluxed for 1 hour
  2. temperaturecooled
  3. concentrationconcentrated
  4. customThe residue was triturated with water
  5. customthe resulting solid was collected
  6. dissolutiondissolved in methanol
  7. custompurified by silica gel chromatography (4% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-5a6c7c89b8044ffdb97805f7dc78146f
Source dataset
uspto-grants-2012_10
Patent number
US08293738B2

Reaction notes

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