Hydrochloric Acid → HCID 86590302, compound

HRID 1977425Notes

Reaction equation

HRID 1977425 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[Cl:8][C:9]1[CH:25]=[CH:24][C:12]([O:13][C:14]2[CH:19]=[N:18][CH:17]=[C:16]3[S:20][C:21]([NH2:23])=[CH:22][C:15]=23)=[CH:11][CH:10]=1.Cl>C(O)=O>[Cl:8][C:9]1[CH:25]=[CH:24][C:12]([O:13][C:14]2[CH:19]=[N:18][CH:17]=[C:16]3[S:20][C:21]([NH:23][CH:1]=[O:3])=[CH:22][C:15]=23)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 9814184HCID 9814184, compound

Product 1

HCID 86590302HCID 86590302, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 5 mL of acetic anhydride and 1.8 mL of 96% formic acid was heated to 70° C. for 3 hours. The solution was allowed to cool whereupon the obtained amine from Example 263 (32 mg, 0.12 mmol) was added. The mixture was stirred for 4 days and then poured into 50 mL of dilute HCl. The mixture was extracted with ethyl acetate, the combined extracts were washed with saturated sodium carbonate and then water, dried (MgSO4), and evaporated. Purification of the resulting product by preparative HPLC using a gradient of 30%-70% acetonitrile/water +0.1% TFA over 40 minutes afforded 18 mg (49%) of the title compound.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe combined extracts were washed with saturated sodium carbonate
  4. dry with materialwater, dried (MgSO4)
  5. customevaporated
  6. customPurification of the resulting product by preparative HPLC
  7. customover 40 minutes

Sources & evidence

ORD record
ord-c1ddff6dbd0d4f3dbcb1958f16fff465
Source dataset
uspto-grants-2001_05
Patent number
US06232320B1

Reaction notes

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