HCID 21907550, compound → HCID 21907514, compound

HRID 1247466Notes

Reaction equation

HRID 1247466 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][NH:9][C:10]2=[O:13])=[C:6]([C:14]2[CH:19]=[CH:18][C:17]([NH:20]C(=O)OC(C)(C)C)=[CH:16][CH:15]=2)[CH:5]=1)([O-:3])=[O:2]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:20][C:17]1[CH:16]=[CH:15][C:14]([C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[C:11]3[C:7]=2[CH2:8][NH:9][C:10]3=[O:13])=[CH:19][CH:18]=1

Participants

4

Reactant 1

HCID 21907550HCID 21907550, compound

Product 1

HCID 21907514HCID 21907514, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 4-(6-nitro-1-oxo-2,3-dihydro-1H-isoindol-4-yl)phenylcarbamate (0.276 g, prepared by substituting Example 128B for Example 1A in Examples 1B and 1C) in TFA (3 mL) and CH2Cl2 (3 mL) was stirred at room temperature for 1 hour, then concentrated to give 0.085 g of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 4.66 (s, 2H), 5.50 (s, 2H), 6.70 (d, J=8.5 Hz, 1H), 7.40 (d, J=8.8 Hz, 2H), 8.20 (d, J=2.0 Hz, 1H), 8.30 (d, J=2.0 Hz, 1H), 9.03 (s, 1H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-24a1e9c61aca45638fce83d0f13931a5
Source dataset
uspto-grants-2006_10
Patent number
US07129260B2

Reaction notes

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