Hydrochloric Acid → HCID 86658104, compound

HRID 245499Notes

Reaction equation

HRID 245499 reaction equation
[Si]([O:18][CH2:19][C:20]1[C:21]([N:37]2[CH2:42][C@H:41]([CH3:43])[O:40][C@H:39]([CH3:44])[CH2:38]2)=[C:22]([F:36])[C:23]2[O:27][N:26]=[C:25]([C:28]3[CH:33]=[N:32][CH:31]=[C:30]([Cl:34])[N:29]=3)[C:24]=2[CH:35]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.Cl>C(O)C.CCOC(C)=O>[Cl:34][C:30]1[N:29]=[C:28]([C:25]2[C:24]3[CH:35]=[C:20]([CH2:19][OH:18])[C:21]([N:37]4[CH2:42][C@H:41]([CH3:43])[O:40][C@H:39]([CH3:44])[CH2:38]4)=[C:22]([F:36])[C:23]=3[O:27][N:26]=2)[CH:33]=[N:32][CH:31]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86658105HCID 86658105, compound2×

Product 1

HCID 86658104HCID 86658104, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

5-((tert-Butyldiphenylsilyloxy)methyl)-3-(6-chloropyrazin-2-yl)-6-((2R,6S)-2,6-dimethylmorpholino)-7-fluorobenzo[d]isoxazole (Intermediate 329, 320 mg, 0.51 mmol) was dissolved in ethanol (10 ml) and was treated with 15 ml of 10% aq HCl, the mixture was heated at 70° C. for 1 hour. The reaction was cooled and diluted with EtOAc before being quenched with aqueous sodium bicarbonate solution. The mixture was extracted with EtOAc, which was washed with brine, dried (MgSO4) and concentrated.

Workup

  1. temperatureThe reaction was cooled
  2. custombefore being quenched with aqueous sodium bicarbonate solution
  3. extractionThe mixture was extracted with EtOAc, which
  4. washwas washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5f6ffc4841fd42ccaf4ea3badb5dd711
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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