Diisopropylethylamine → HCID 140448329, compound

HRID 1840604Notes

Reaction equation

HRID 1840604 reaction equation
Cl.[C:2]([C:5]1[CH:32]=[CH:31][C:8]([CH2:9][N:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[CH2:20][O:21][C:22]4[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:23]=4[CH:24]=3)(=[O:18])=[O:17])[CH2:12][C:11]2=[O:30])=[CH:7][CH:6]=1)(=[NH:4])[NH2:3].[C:33]([O:36][CH:37]([O:39][C:40](OC1C=CC([N+]([O-])=O)=CC=1)=[O:41])[CH3:38])(=[O:35])[CH3:34].C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:33]([O:36][CH:37]([O:39][C:40]([NH:4][C:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[CH2:20][O:21][C:22]4[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:23]=4[CH:24]=3)(=[O:18])=[O:17])[CH2:12][C:11]2=[O:30])=[CH:31][CH:32]=1)=[NH:3])=[O:41])[CH3:38])(=[O:35])[CH3:34]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 117805601-acetoxyethyl p-nitrophenyl carbonateHCID 23447334HCID 23447334, compound

Product 1

HCID 140448329HCID 140448329, compoundYield 41.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(4-amidinobenzyl)-4-(7-chloro-2H-benzopyran-3-sulfonyl)-2-piperazinone hydrochloride (99 mg), O-(1-acetoxyethoxycarbonyl)-4-nitrophenol (54 mg), diisopropylethylamine (39 mg) in DMF (5 ml) was stirred at 80° C. for 1 hour. The reaction solution was concentrated under reduced pressure, and to the residue was added ethyl acetate. The mixture was washed with sodium bicarbonate solution and saturated brine, dried (MgSO4) and concentrated. Precipitated crystals were washed with ether to give colorless crystals of the title compound (49 mg).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionto the residue was added ethyl acetate
  3. washThe mixture was washed with sodium bicarbonate solution and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPrecipitated crystals
  7. washwere washed with ether

Sources & evidence

ORD record
ord-3a9bdd9856954b66bc6fbfb769bbb732
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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