Isoniazid → HCID 67070926, compound

HRID 273163Notes

Reaction equation

HRID 273163 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([CH2:13][CH:14]3[CH2:19][CH2:18][CH2:17][NH:16][C:15]3=O)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:21]([NH:29][NH2:30])(=O)[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([CH2:13][CH:14]3[CH2:19][CH2:18][CH2:17][N:16]4[C:21]([C:22]5[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=5)=[N:29][N:30]=[C:15]34)[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3767IsoniazidHCID 67070935HCID 67070935, compound

Product 1

HCID 67070926HCID 67070926, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

37 mg (0.25 mmol) Me3OBF4 was added to a solution of 60 mg (0.21 mmol) 3-[5-(3-chloro-phenyl)-[1,2,4]oxadiazol-3-ylmethyl]-piperidin-2-one in 2 ml CH2Cl2. The mixture was stirred overnight at room temperature. The reaction mixture was diluted with CH2Cl2, washed with NaHCO3 (sat), dried and concentrated. The residue was dissolved in 3 ml EtOH and 22 mg (0.16 mmol) isonicotinic hydrazide was added. The solution was heated with microwaves at 120° C. for 10 min. The reaction mixture was cooled and the volatiles were removed under reduced pressure. The crude product was purified by preparative HPLC to afford 17 mg (20%) of the desired product. 1H NMR (CDCl3): d ppm 1.75 (m, 1 H) 1.99 (m, 1 H) 2.21 (m, 2 H) 3.16 (dd, 1 H) 3.73 (m, 1 H) 3.85 (dd, 1 H) 4.07 (m, 1 H) 4.19 (m, 1 H) 7.47 (t, 1 H) 7.56 (m, 1 H) 7.67 (m, 2 H) 8.01 (m, 1 H) 8.11 m, 1 H) 8.76 (d, 2 H).

Workup

  1. washwashed with NaHCO3 (sat)
  2. customdried
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in 3 ml EtOH
  5. temperatureThe solution was heated with microwaves at 120° C. for 10 min
  6. temperatureThe reaction mixture was cooled
  7. customthe volatiles were removed under reduced pressure
  8. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-5a5740da16814959872fce5ab8504340
Source dataset
uspto-grants-2008_11
Patent number
US07456200B2

Reaction notes

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