Acetic Acid → HCID 178509408, compound

HRID 2402439Notes

Reaction equation

HRID 2402439 reaction equation
[C:1]([C:3]1[C:4]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])=[C:5]([C:15]([NH2:17])=O)[S:6][C:7]=1[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([F:14])[CH:9]=1)#[N:2].COC(OC)[N:29]([CH3:31])C.C(O)(=O)C.O.[NH2:39]N>>[Cl:25][C:19]1[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=1[C:4]1[C:3]([C:1]#[N:2])=[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([F:14])[CH:9]=2)[S:6][C:5]=1[C:15]1[NH:29][CH:31]=[N:39][N:17]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetalHCID 46866575HCID 46866575, compound

Product 1

HCID 178509408HCID 178509408, compoundYield 93.9%

Conditions

Temperature
85 °C

Procedure

A mixture of 4-cyano-3-(2,4-dichlorophenyl)-5-(2-fluoropyridin-4-yl)thiophene-2-carboxamide (0.90 g, 0.0022 mol) in 1,1-dimethoxy-N,N-dimethylmethanamine (5.50 g, 0.045 mol) was stirred at 85° C. overnight. The mixture was evaporated to dryness and the residue was dissolved in acetic acid (14 mL, 0.2 mol) and hydrazine hydrate (1.4 mL, 0.02 mol) was added. The mixture was stirred at 85° C. for 5 hours. The solvent was removed and the residue was suspended in water. The precipitate was collected and dried in an oven to afford the product (0.86 g, 90%). LCMS: (FA) ES+, 416, 418. 1H NMR (400 MHz, d4-Methanol) 8.42 (s, 1H), 8.41 (d, J=5.21 Hz, 1H), 7.81 (td, J=5.33, 1.58, 1.58 Hz, 1H), 7.63 (t, J=1.18, 1.18 Hz, 1H), 7.60 (s, 1H), 7.48-7.46 (m, 2H).

Workup

  1. customThe mixture was evaporated to dryness
  2. stirringThe mixture was stirred at 85° C. for 5 hours
  3. customThe solvent was removed
  4. customThe precipitate was collected
  5. customdried in an oven

Sources & evidence

ORD record
ord-0c9eb5fe7bb34495a9f0f45b14322968
Source dataset
uspto-grants-2014_08
Patent number
US08796314B2

Reaction notes

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