Triethylamine hydrochloride → HCID 53390437, compound

HRID 889378Notes

Reaction equation

HRID 889378 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl.C(N(CC)CC)C.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:24]([CH:25]([CH:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)[CH2:26][O:27][C:28]3[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][C:29]=3[F:36])=[C:23]3[CH2:43][CH2:44][CH2:45][C:22]3=[N:21]2)=[CH:16][CH:15]=1>CN(C=O)C>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:24]([CH:25]([CH:37]3[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]3)[CH2:26][O:27][C:28]3[CH:35]=[CH:34][C:31]([C:32]4[N:1]=[N:2][NH:3][N:33]=4)=[CH:30][C:29]=3[F:36])=[C:23]3[CH2:43][CH2:44][CH2:45][C:22]3=[N:21]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 53390253HCID 53390253, compound

Product 1

HCID 53390437HCID 53390437, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Sodium azide (14 mg, 215 umol) and triethylamine hydrochloride (29 mg, 215 umol) were added to a solution of 4-{2-[2-(4-chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-2-cyclohexyl-ethoxy}-3-fluoro-benzonitrile (20 mg, 43 umol; example 3) in DMF (0.5 ml). The solution was stirred at 120° C. for 14 h, poured onto ice water/1 N aqueous HCl solution 1/1 and extracted two times with iPrOAc. The combined extracts were washed with ice water/brine 1/1 and dried over Na2SO4. The solvent was removed under reduced pressure to give a solid which was crystallized from heptane/dichloromethane to obtain the title compound (13 mg, 26 umol; 59%) as off-white solid. MS: m/e=507.2 [M+H+].

Workup

  1. additionpoured onto ice water/1 N aqueous HCl solution 1/1
  2. extractionextracted two times with iPrOAc
  3. washThe combined extracts were washed with ice water/brine 1/1
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customto give a solid which
  7. customwas crystallized from heptane/dichloromethane

Sources & evidence

ORD record
ord-6e48295e6cc44f41a8accf4d3d85f7d1
Source dataset
uspto-grants-2012_08
Patent number
US08252826B2

Reaction notes

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