Sodium hydride → 9-{[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]methyl}-3-pyridin-4-yl-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a][1,3]diazepine

HRID 2102309Notes

Reaction equation

HRID 2102309 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]3[CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:12]3=[N:11][N:10]=2)=[CH:5][CH:4]=1.Cl[CH2:20][C:21]1[N:25]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=2)[O:23][N:22]=1.[NH4+].[Cl-]>CN(C=O)C>[Cl:32][C:28]1[CH:27]=[C:26]([C:24]2[O:23][N:22]=[C:21]([CH2:20][N:18]3[CH2:17][CH2:16][CH2:15][CH2:14][N:13]4[C:9]([C:6]5[CH:7]=[CH:8][N:3]=[CH:4][CH:5]=5)=[N:10][N:11]=[C:12]34)[N:25]=2)[CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 100825203-(Chloromethyl)-5-(3-chlorophenyl)-1,2,4-oxadiazoleHCID 1361224673-(Pyridin-4-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a][1,3]diazepine

Product 1

HCID 113503199-{[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]methyl}-3-pyridin-4-yl-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a][1,3]diazepineYield 54.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (65 mg, 0.28 mmol) was added to a solution of 3-pyridin-4-yl-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a][1,3]diazepine (54 mg, 0.25 mmol) in DMF (5 ml). After 10 min 3-(chloromethyl)-5-(3-chlorophenyl)-1,2,4-oxadiazole (65 mg, 0.28 mmol) was added at r.t. Stirring was continued o.n. and NH4Cl solution, sat., was added and the mixture was extracted with EA. The organic phase was dried and concentrated. Flash chromatography (DCM/MeOH 20:1) yielded 56 mg (54%) of the title compound. 1H NMR: 1.89-2.01 (m, 4H), 3.33-3.42 (m, 2H), 3.90-3.98 (m, 2H), 4.88 (s, 2H), 7.42-7.49 (m, 3H), 7.53 (m, 1H), 7.98 (m, 1H), 8.09 (m, 1H), 8.71 (d, 2H).

Workup

  1. extractionthe mixture was extracted with EA
  2. customThe organic phase was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5f46c28e059e436dbf57607b7f92b56e
Source dataset
uspto-grants-2009_08
Patent number
US07576077B2

Reaction notes

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