Hydrochloric Acid → HCID 57412143, compound

HRID 535898Notes

Reaction equation

HRID 535898 reaction equation
[C:1]([C:4]1[C:9]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]3)=[CH:13][C:12]=2[O:30][CH3:31])=[CH:8][C:7]([CH2:32][C:33]2[C:38]([Cl:39])=[CH:37][CH:36]=[CH:35][C:34]=2[Cl:40])=[CH:6][N:5]=1)(=[O:3])[NH2:2].Cl>O1CCOCC1>[Cl:40][C:34]1[CH:35]=[CH:36][CH:37]=[C:38]([Cl:39])[C:33]=1[CH2:32][C:7]1[CH:8]=[C:9]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[CH:13][C:12]=2[O:30][CH3:31])[C:4]([C:1]([NH2:2])=[O:3])=[N:5][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70497663HCID 70497663, compound

Product 1

HCID 57412143HCID 57412143, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of the product of EXAMPLE 1C (76 mg, 0.13 mmol) in dioxane (1 mL) was treated with 4N HCl in dioxane (1 mL) and stirred at ambient temperature for 3 hours. The reaction mixture was concentrated under reduced pressure; and the residue was neutralized with 1N aqueous NaOH and extracted with dichloromethane. The organics were washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. Purification by silica gel chromatography (0-10% methanol in dichloromethane) provided the title compound. 1H NMR (DMSO-d6) δ ppm 2.85 (t, 4H, J=5.2 Hz), 3.05 (t, 4H, J=5.2 Hz), 3.66 (s, 3H), 4.19 (s, 2H), 6.39-6.42 (m, 1H), 6.57 (s, 1H), 6.88-6.97 (m, 2H), 7.33 (t, 1H, J=8.4 Hz), 7.48-7.51 (m, 3H), 7.73 (s, 1H), 8.06 (s, 1H), 9.88 (s, 1H); MS (ESI) m/z 487 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with dichloromethane
  3. washThe organics were washed with brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by silica gel chromatography (0-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-df8e66b1dcc94186a2a9bab88fbada33
Source dataset
uspto-grants-2014_10
Patent number
US08859546B2

Reaction notes

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