Isonicotinoyl chloride hydrochloride → 3-(Pyridin-4-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a][1,3]diazepine

HRID 2102290Notes

Reaction equation

HRID 2102290 reaction equation
I.[NH:2]1[CH2:8][CH2:7][CH2:6][CH2:5][NH:4][C:3]1=[N:9][NH2:10].Cl.[C:12](Cl)(=O)[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1>>[N:16]1[CH:17]=[CH:18][C:13]([C:12]2[N:2]3[CH2:8][CH2:7][CH2:6][CH2:5][NH:4][C:3]3=[N:9][N:10]=2)=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 12262826Isonicotinoyl chloride hydrochlorideHCID 178506609HCID 178506609, compound

Product 1

HCID 1361224673-(Pyridin-4-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a][1,3]diazepineYield 207.3%

Conditions

Temperature
160 °C

Procedure

A mixture of 1,3-diazepan-2-one hydrazone hydroiodide(1.00 g, 3.9 mmol) and isonicotinoyl chloride hydrochloride (695 mg, 3.9 mmol) was heated in a microwave reactor at 160° C. for 10 min. The reaction mixture was poured into NaaCO3 solution, sat., and extracted with DCM. The organic phase was dried and concentrated. Flash chromatography (DCM/MeOH 20:1) gave 1.74 g crude title compound which was used directly in the next step. 1H NMR: 1.89 (s, 4H), 3.15 (m, 2H), 3.86 (m, 2H), 7.44 (d, 2H), 8.66 (d, 2H).

Workup

  1. additionThe reaction mixture was poured into NaaCO3 solution
  2. extractionsat., and extracted with DCM
  3. customThe organic phase was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3c0629cb046b441fad17a854fffb6d82
Source dataset
uspto-grants-2009_08
Patent number
US07576077B2

Reaction notes

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