Acetic Acid → HCID 58269033, compound

HRID 1428186Notes

Reaction equation

HRID 1428186 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]([S:17][CH3:18])[N:14]=[C:13]([CH:19]([C:22]#[N:23])[C:20]#[N:21])[CH:12]=2)[CH3:9])=[CH:4][CH:3]=1.[NH2:24][NH2:25].C(O)(=O)C.[CH3:30][CH:31](O)[CH3:32]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]([S:17][CH3:18])[N:14]=[C:13]([C:19]3[C:20]([NH2:21])=[N:24][N:25]4[CH:32]=[CH:31][CH:30]=[N:23][C:22]=34)[CH:12]=2)[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 3776IsopropanolHCID 9321HydrazineHCID 86653541HCID 86653541, compound

Product 1

HCID 58269033HCID 58269033, compound

Conditions

Temperature
160 °C

Procedure

(1(S)-2-(6-(1-(4-Fluorophenyl)ethylamino)-2-(methylthio)pyrimidin-4-yl)malononitrile (16c, 110 mg, 0.33 mmol) was suspended in IPA (6.0 mL). Hydrazine was then added (11.0 mg, 0.34 mmol). The reaction mixture was heated at 160° C. with microwave irradiation. After 10 minutes, the reaction mixture was allowed to cool to rt. LC/MS showed the presence of product (LC/MS (M+1): 360.5). In the same pot, glacial acetic acid (130 mg) was added, followed by N,N-dimethyl acrolein (130 mg, 1.3 mmol). The reaction mixture was heated at 160° C. with microwave irradiation for 10 minutes. The mixture was then allowed to cool down to rt. All volatiles were removed at reduced pressure and the crude residue was purified on a combi-flash system (0-100% Hexane/EtOAc). Yield: 55 mg (45%) of the title compound.

Workup

  1. temperatureto cool to rt
  2. temperatureThe reaction mixture was heated at 160° C. with microwave irradiation for 10 minutes
  3. temperatureto cool down to rt
  4. customAll volatiles were removed at reduced pressure
  5. customthe crude residue was purified on a combi-flash system (0-100% Hexane/EtOAc)

Sources & evidence

ORD record
ord-1bbfdde6ceae47139449c75a054cea53
Source dataset
uspto-grants-2015_01
Patent number
US08937064B2

Reaction notes

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