Acetic Acid → HCID 66604593, compound

HRID 2410703Notes

Reaction equation

HRID 2410703 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[O:23])=[CH:18][CH:17]=3)=[C:11]([C:30]#[N:31])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].CC(O)=[O:34]>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([C:30]([NH2:31])=[O:34])[C:12]3[NH:15][C:16]4[C:17]([C:13]=3[CH:14]=2)=[CH:18][C:19]([C:22]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[O:23])=[CH:20][CH:21]=4)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 66604864HCID 66604864, compound

Product 1

HCID 66604593HCID 66604593, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
130 °C

Procedure

3′,4′-Dimethyl-4-(4-(morpholine-4-carbonyl)phenylamino)biphenyl-3-carbonitrile (320 mg, 0.777 mmol) and Pd(OAc)2 (0.523 g, 2.331 mmol) were mixed with AcOH (10 mL) in a sealed microwave tube and heated at 130° C. for 12 hrs. The mixture was filtered through a pad of CELITE®, then a ACRODISC® PTFE membrane (0.45 um), rinsed with additional 35 ml AcOH. The filtrate was concentrated and purified using preparative HPLC to give 51.8 mg of titled product. MS (ESI) m/z 428.4 (M+H)+. 1H NMR (DMSO-d6) δ ppm 11.59 (s, 1H), 8.74 (s, 1H), 8.38 (bs, 2H), 8.3 (s, 1H), 7.76(d, 1H, J=8.2), 7.71 (s, 1H), 7.63 (d, 1H, J=6.3), 7.57 (bs, 1H), 7.48(d, 1H, J=8.2), 7.27(d, 1H, J=7.6), 3.65-3.59 (bm, 8H), 2.35 (s, 3H),), 2.29 (s, 3H).

Workup

  1. filtrationThe mixture was filtered through a pad of CELITE®
  2. washa ACRODISC® PTFE membrane (0.45 um), rinsed with additional 35 ml AcOH
  3. concentrationThe filtrate was concentrated
  4. custompurified

Sources & evidence

ORD record
ord-436110211e6841fd849132ddb6e177f3
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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