Acetic Acid → HCID 58094733, compound

HRID 2282146Notes

Reaction equation

HRID 2282146 reaction equation
[C:1]([C:4]1[S:8][C:7]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([F:15])[CH:10]=2)=[C:6]([C:16]#[N:17])[C:5]=1[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])(=O)[CH3:2].COC(OC)[N:29]([CH3:31])C.CC(O)=O.O.[NH2:39]N>>[Cl:25][C:19]1[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=1[C:5]1[C:6]([C:16]#[N:17])=[C:7]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([F:15])[CH:10]=2)[S:8][C:4]=1[C:1]1[NH:39][N:29]=[CH:31][CH:2]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetalHCID 58094890HCID 58094890, compound

Product 1

HCID 58094733HCID 58094733, compoundYield 79%

Conditions

Temperature
90 °C

Procedure

A solution of [A] 5-acetyl-4-(2,4-dichlorophenyl)-2-(2-fluoropyridin-4-yl)thiophene-3-carbonitrile (0.407 g, 1.04 mmol) in 1,1-Dimethoxy-N,N-dimethylmethanamine (5.53 mL, 41.6 mmol) was irradiated in microwave at 120° C. for 20 min. The solvent was removed and the residue was taken up by AcOH (21 mL, 370 mmol). Hydrazine hydrate (3 mL, 60 mmol) was added the above mixture and then heated at 90° C. for 10 min. The mixture was concentrated and the residue was suspended in water. The precipitated was collected and dried in air to afford the title compound as a yellow powder (0.34 g, 79%). LC/MS (FA) ES+ 415, 417. 1H NMR (400 MHz, d4-methanol) δ: 8.45 (1H, d, J=5.33 Hz), 7.85 (1H, td, J=5.32, 1.57, 1.57 Hz), 7.80 (1H, d, J=1.99 Hz), 7.54 (1H, d, J=8.24 Hz), 7.60 (1H, dd, J=8.27, 2.04 Hz), 7.63 (2H, d, J=2.47 Hz), 5.69 (1H, d, J=2.44 Hz)

Workup

  1. customThe solvent was removed
  2. concentrationThe mixture was concentrated
  3. customThe precipitated was collected
  4. customdried in air

Sources & evidence

ORD record
ord-8df4b729e3574ef680a31579befc3b42
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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