HCID 10380860, compound → HCID 10244180, compound

HRID 1613630Notes

Reaction equation

HRID 1613630 reaction equation
C([N:5]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[S:6]1(=[O:21])=[O:20])(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[N+:17]([C:14]1[CH:15]=[CH:16][C:11]([CH2:10][N:7]2[CH2:8][CH2:9][NH:5][S:6]2(=[O:21])=[O:20])=[CH:12][CH:13]=1)([O-:19])=[O:18]

Participants

4

Reactant 1

HCID 10380860HCID 10380860, compound

Product 1

HCID 10244180HCID 10244180, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the product from Step 1 (1.5 g) in anhydrous dichloromethane (10 ml) and trifluoroacetic acid (10 ml) was allowed to stand at room temperature for 48 hours. Solvents were removed under vacuum and the remaining residue was azeotroped with methanol (1×25 ml) and crystallised from ethyl acetate-hexane to give 966 mg (78%) of the title compound as a pale yellow solid; mp 115°-117° C.; δH (250 MHz, CDCl3) 8.23 (2H, d, J=8.8 Hz, Ar--H), 7.57 (2H, d, J=8.8 Hz, Ar--H), 4.38 (1H, br t, --NH--), 4.29 (2H, s, Ar--CH2 --), 3.54 (2H, q, J=6.6 Hz, --CH2 --NH--), 3.34 (2H, t, J=6.6 Hz, --CH2 --).

Workup

  1. customSolvents were removed under vacuum
  2. customthe remaining residue was azeotroped with methanol (1×25 ml)
  3. customcrystallised from ethyl acetate-hexane

Sources & evidence

ORD record
ord-7ab6ddeac0ee4403a5ebe024900a9d80
Source dataset
uspto-grants-1993_03
Patent number
US05194440

Reaction notes

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