Triethylamine hydrochloride → HCID 56644217, compound

HRID 1526695Notes

Reaction equation

HRID 1526695 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]([C:19]#[N:20])[CH:17]=[CH:18][C:13]=3[N:12]3[C:21]([CH3:24])=[N:22][N:23]=[C:11]3[C@H:10]([CH2:25][C:26]([NH:28][CH2:29][CH3:30])=[O:27])[N:9]=2)=[CH:4][CH:3]=1.Cl.C(N(CC)CC)C.[N-:39]=[N+:40]=[N-:41].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]([C:19]4[N:39]=[N:40][NH:41][N:20]=4)[CH:17]=[CH:18][C:13]=3[N:12]3[C:21]([CH3:24])=[N:22][N:23]=[C:11]3[C@H:10]([CH2:25][C:26]([NH:28][CH2:29][CH3:30])=[O:27])[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 68003909HCID 68003909, compound

Product 1

HCID 56644217HCID 56644217, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

(S)-2-(6-(4-Chlorophenyl)-8-cyano-1-methyl-4H-benzo[f][1,2,4]triazolo[4,3-a][1,4]diazepin-4-yl)-N-ethylacetamide (for a preparation see Intermediate 7) (68.4 mg) was dissolved in DMF (5 ml). Triethylamine hydrochloride (45.0 mg) and sodium azide (21.23 mg) were added and the reaction mixture was heated at 100° C., under nitrogen, overnight. The temperature was raised to 120° C. and the reaction mixture was heated overnight. The reaction mixture was allowed to cool to room temperature, partitioned between ethyl acetate and water. The organic phase was washed with water (2×10 ml) and brine (10 ml). The aqueous layer was passed through a pre equilibrated Biotage 103 column. The organic content was eluted with methanol, the methanolic solution was evaporated and the residue was chromatographed (10-20% methanol:DCM). Trituration with diethyl ether gave (S)-2-(6-(4-chlorophenyl)-1-methyl-8-(2H-tetrazol-5-yl)-4H-benzo[f][1,2,4]triazolo[4,3-a][1,4]diazepin-4-yl)-N-ethylacetamide (25.6 mg) as a yellow solid. LCMS (formate): MH+ 462/464, RT 0.75 min

Workup

  1. temperatureThe temperature was raised to 120° C.
  2. temperaturethe reaction mixture was heated overnight
  3. temperatureto cool to room temperature
  4. custompartitioned between ethyl acetate and water
  5. washThe organic phase was washed with water (2×10 ml) and brine (10 ml)
  6. washThe organic content was eluted with methanol
  7. customthe methanolic solution was evaporated
  8. customthe residue was chromatographed (10-20% methanol:DCM)

Sources & evidence

ORD record
ord-9a89f55804fd4ebeba149c1752b359bf
Source dataset
uspto-grants-2015_07
Patent number
US09085582B2

Reaction notes

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