Hydrochloric Acid → HCID 46178824, compound

HRID 339701Notes

Reaction equation

HRID 339701 reaction equation
[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([N:20]4[CH2:25][CH2:24][C:23]([NH:27]C(=O)OCC5C=CC=CC=5)([CH3:26])[CH2:22][CH2:21]4)[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.Cl>O.C(Cl)Cl>[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([N:20]4[CH2:21][CH2:22][C:23]([CH3:26])([NH2:27])[CH2:24][CH2:25]4)[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67234238HCID 67234238, compound

Product 1

HCID 46178824HCID 46178824, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To the product from Step A (0.115 g, 0.233 mmol) was added HCl (1.17 mL, 7.00 mmol, 6.0N aqueous). The mixture was stirred at 90° C. for 45 minutes. The mixture was then cooled to ambient temperature and diluted with water (10 mL) and with CH2Cl2 (10 mL). The layers were mixed and separated and the aqueous phase was washed once more with CH2Cl2 (10 mL) and was then treated with saturated aqueous Na2CO3 until pH=10. The aqueous phase was then extracted with CH2Cl2 (3×10 mL). The combined organic phases were washed with water followed by brine and then dried over Na2SO4, filtered and concentrated to provide 0.058 g (66%) of the product >96% pure by HPLC. MS ESI (+) m/z 359.1 (M+1) detected.

Workup

  1. temperatureThe mixture was then cooled to ambient temperature
  2. additionThe layers were mixed
  3. customseparated
  4. washthe aqueous phase was washed once more with CH2Cl2 (10 mL)
  5. additionwas then treated with saturated aqueous Na2CO3 until pH=10
  6. extractionThe aqueous phase was then extracted with CH2Cl2 (3×10 mL)
  7. washThe combined organic phases were washed with water
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-fe626c09cf9044be81abc125ccbd7dd9
Source dataset
uspto-grants-2014_11
Patent number
US08895550B2

Reaction notes

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