Diisopropylethylamine → HCID 22710467, compound

HRID 352976Notes

Reaction equation

HRID 352976 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]3[S:24][C:25]4[CH2:26][NH:27][CH2:28][CH2:29][C:30]=4[N:31]=3)=[O:22])[CH:17]([CH2:32][C:33]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)=[O:34])[CH2:16]1)(=[O:14])=[O:13])=[CH:6]2.C(N(C(C)C)CC)(C)C.[C:50](=O)([O:58]C1C=CC([N+]([O-])=O)=CC=1)[O:51][CH:52]([O:54][C:55](=[O:57])[CH3:56])[CH3:53]>C(O)C>[C:55]([O:54][CH:52]([O:51][C:50]([CH:28]1[NH:27][CH2:26][C:25]2[S:24][C:23]([C:21]([N:18]3[CH2:19][CH2:20][N:15]([S:12]([C:7]4[NH:8][C:9]5[C:5]([CH:6]=4)=[CH:4][C:3]([Cl:2])=[CH:11][CH:10]=5)(=[O:13])=[O:14])[CH2:16][CH:17]3[CH2:32][C:33]([N:35]3[CH2:36][CH2:37][O:38][CH2:39][CH2:40]3)=[O:34])=[O:22])=[N:31][C:30]=2[CH2:29]1)=[O:58])[CH3:53])(=[O:57])[CH3:56]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 117805601-acetoxyethyl p-nitrophenyl carbonateHCID 22709979HCID 22709979, compound

Product 1

HCID 22710467HCID 22710467, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (6 ml) was dissolved 4-[(5-chloroindol-2-yl)sulfonyl]-2-[[(morpholin-4-yl)carbonyl]methyl]-1-[(4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]piperazine hydrochloride (200 mg), followed by the addition of diisopropylethylamine (83 μl) and 1-acetoxyethyl p-nitrophenyl carbonate (128 mg). The resulting mixture was stirred at room temperature for 5 hours. The solvent was distilled off under reduced pressure. Methylene chloride and an aqueous solution of sodium bicarbonate were added and the mixture was separated into layers. The organic layer was dried over anhydrous sodium sulfate and the filtrate was concentrated. The residue was purified by chromatography on a silica gel column (1-2% methanol-methylene chloride). The product was dissolved in ethyl acetate, followed by crystallization from diethyl ether, whereby the title compound (100 mg) was obtained as colorless powder.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionMethylene chloride and an aqueous solution of sodium bicarbonate were added
  3. customthe mixture was separated into layers
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by chromatography on a silica gel column (1-2% methanol-methylene chloride)
  7. dissolutionThe product was dissolved in ethyl acetate
  8. customfollowed by crystallization from diethyl ether, whereby the title compound (100 mg)
  9. customwas obtained as colorless powder

Sources & evidence

ORD record
ord-472e53be61b049b898b10733d06c906d
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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