Hydrochloric Acid → HCID 67234157, compound

HRID 339707Notes

Reaction equation

HRID 339707 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@H:23]([NH:26]C(=O)OCC5C=CC=CC=5)[C@H:22]([F:37])[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[CH2:25][CH2:24][CH:23]([NH2:26])[CH:22]([F:37])[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

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131730904HCID 131730904, compound

Product 1

HCID 67234157HCID 67234157, compoundYield 69.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To the product from Step G (0.185 g, 0.373 mmol) was added HCl (1.86 mL, 11.2 mmol, 6.0M aqueous) and the solution was warmed to 90° C. and stirred for 0.5 hours. The mixture was 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 treated with saturated aqueous Na2CO3 until pH=10. The aqueous phase was extracted with CH2Cl2 (4×10 mL). The combined organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated. The crude residue was purified by column chromatography (1 to 10% MeOH w/6% NH4OH/CH2Cl2) to afford 0.094 g (69%) of the desired product as a pale yellow/orange solid. MS ESI (+) m/z 363.2 (M+1) detected.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. additionThe layers were mixed
  3. customseparated
  4. additionthe aqueous phase was treated with saturated aqueous Na2CO3 until pH=10
  5. extractionThe aqueous phase was extracted with CH2Cl2 (4×10 mL)
  6. washThe combined organic phase was washed with water and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude residue was purified by column chromatography (1 to 10% MeOH w/6% NH4OH/CH2Cl2)

Sources & evidence

ORD record
ord-56bde4d83f4640cbae735269225b22b5
Source dataset
uspto-grants-2014_11
Patent number
US08895550B2

Reaction notes

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