Triethylamine hydrochloride → HCID 45111057, compound

HRID 1678661Notes

Reaction equation

HRID 1678661 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:28]([CH:29]([CH:41]3[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]3)[CH2:30][O:31][C:32]3[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[CH:34][C:33]=3[F:40])=[C:27]3[C:22]([CH:23]=[CH:24][CH:25]=[CH:26]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:28]([CH:29]([CH:41]3[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]3)[CH2:30][O:31][C:32]3[CH:39]=[CH:38][C:35]([C:36]4[N:1]=[N:2][NH:3][N:37]=4)=[CH:34][C:33]=3[F:40])=[C:27]3[C:22]([CH:23]=[CH:24][CH:25]=[CH:26]3)=[N:21]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 45111056HCID 45111056, compound

Product 1

HCID 45111057HCID 45111057, compoundYield 37.2%

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 [rac]-4-{2-[2-(4-chloro-phenyl)-2H-indazol-3-yl]-2-cyclohexyl-ethoxy}-3-fluoro-benzonitrile (20 mg, 43 umol; example 30) in DMF (0.4 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 acetonitrile to obtain the title compound (8 mg, 16 umol; 37%) as off-white solid. MS: m/e=518.0 [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 acetonitrile

Sources & evidence

ORD record
ord-95e817cd18cc42e39478e7c4ea6db04c
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

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