HCID 69045865, compound → HCID 22171015, compound

HRID 2376240Notes

Reaction equation

HRID 2376240 reaction equation
C([O:5][C:6](=[O:39])[CH:7]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([N:36]([CH3:38])[CH3:37])[CH:31]=1)[CH2:8][C:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[N:11]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[Cl:29])[N:10]=1)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[Cl:21][C:16]1[CH:15]=[C:14]([C:12]2[N:11]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[Cl:29])[N:10]=[C:9]([CH2:8][CH:7]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([N:36]([CH3:38])[CH3:37])[CH:31]=3)[C:6]([OH:39])=[O:5])[CH:13]=2)[CH:19]=[CH:18][C:17]=1[Cl:20]

Participants

3

Reactant 1

HCID 69045865HCID 69045865, compound

Product 1

HCID 22171015HCID 22171015, compoundYield 109.2%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

3-[5-(3,4-Dichloro-phenyl)-1-(2,4-dichloro-phenyl)-1H-pyrazol-3-yl]-2-(3-dimethylamino-phenyl)-propionic acid tert-butyl ester (20 mg, 0.03 mmol) was dissolved in 1:1 trifluoroacetic acid/dichloromethane (1.0 mL) and stirred for 2 h. The reaction mixture was concentrated under reduced pressure, and the crude residue was dissolved in 1:1 acetonitrile/water (2.0 mL). The solution was lyopholized to afford the title compound (18 mg, >99%). HPLC: Rt=2.60 (Method B). MS (ESI): mass calculated for C26H21Cl4N3O2, 547.04; m/z found, 548/550[M+H]+. 1H NMR (500 MHz, DMSO-d6): 7.81 (d, J=1.9 Hz, 1H), 7.60-7.58 (m, 3H), 7.45 (d, J=2.2 Hz, 1H), 7.18 (t, J=7.9 Hz, 1H), 7.02 (dd, J=8.5, 2.2 Hz, 1H), 6.78 (m, 3H), 6.64 (s, 1H), 3.96 (dd, J=8.8, 6.6 Hz, 1H), 3.36 (dd, J=15.1, 9.0 Hz, 1H), 2.93 (dd, J=15.1, 6.6 Hz, 1H), 2.91 (s, 6H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe crude residue was dissolved in 1:1 acetonitrile/water (2.0 mL)

Sources & evidence

ORD record
ord-4db0d5c96fe64b85bec8038dc05cd36f
Source dataset
uspto-grants-2008_12
Patent number
US07465808B2

Reaction notes

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