Hydrochloric Acid → HCID 22727075, compound

HRID 2086280Notes

Reaction equation

HRID 2086280 reaction equation
[Br:1][C:2]1[CH:28]=[CH:27][C:5]2[CH:6]=[C:7]([S:10]([N:13]3[CH2:18][CH2:17][N:16]([NH:19][CH:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[C:15](=[O:26])[CH2:14]3)(=[O:12])=[O:11])[CH2:8][O:9][C:4]=2[CH:3]=1.[CH2:29]([N:31](CC)CC)[CH3:30].[ClH:36].C(=N)(OCC)C.Cl>CO.C(OCC)(=O)C>[ClH:36].[ClH:36].[C:29]([N:23]1[CH2:24][CH2:25][CH:20]([NH:19][N:16]2[CH2:17][CH2:18][N:13]([S:10]([C:7]3[CH2:8][O:9][C:4]4[CH:3]=[C:2]([Br:1])[CH:28]=[CH:27][C:5]=4[CH:6]=3)(=[O:11])=[O:12])[CH2:14][C:15]2=[O:26])[CH2:21][CH2:22]1)(=[NH:31])[CH3:30]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 22727289HCID 22727289, compound

Product 1

HCID 22727075HCID 22727075, compoundYield 188.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 4-(7-bromo-2H-benzopyran-3-sulfonyl)-1-(4-piperidinylamino)-2-piperazinone (104 mg) and triethylamine (272 mg) in methanol (10 ml) was combined with ethyl acetoimidate hydrochloride (272 mg) and stirred at room temperature for 3 hours. The reaction mixture was concentrated and the residue was dissolved in dichloromethane, washed with a 1N aqueous solution of sodium hydroxide and brine, dried and concentrated. The residue obtained was suspended in ethyl acetate, combined with a 4N solution of hydrochloric acid in ethyl acetate to precipitate a hydrochloride, which was collected by filtration and dried to obtain the title compound (243 mg) as a colorless solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with a 1N aqueous solution of sodium hydroxide and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue obtained
  7. customto precipitate a hydrochloride, which
  8. filtrationwas collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-dba24265b64e4ecc89d1047b0fc81afb
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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