Ammonium Chloride → HCID 178521903, compound

HRID 1678686Notes

Reaction equation

HRID 1678686 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([CH:17]([CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][C:22]=3[F:29])=[O:19])=[C:15]3[C:10]([CH2:11][CH2:12][CH2:13][CH2:14]3)=[N:9]2)=[CH:4][CH:3]=1.[NH4+].[Cl-].[N-:38]=[N+:39]=[N-:40].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]([CH:17]([CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[NH:40][N:39]=[N:38][N:28]=4)=[CH:23][C:22]=3[F:29])=[O:19])=[C:15]3[C:10]([CH2:11][CH2:12][CH2:13][CH2:14]3)=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 67130988HCID 67130988, compound

Product 1

HCID 178521903HCID 178521903, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of [rac]-2-[2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-N-(4-cyano-2-fluoro-phenyl)-2-cyclohexyl-acetamide (110 mg, 0.22 mmol) in dry DMF (3 ml) was added NH4Cl (48.39 mg, 0.88 mmol) and NaN3 (57.2 mg, 0.88 mmol) at room temperature. The reaction mixture was then heated at 120° C. for 12 h. After cooling, TLC shows formation of new spot, filtered the solid material by sintered funnel and washed the solid residue by EtOAc (3×5 ml). Combined organic layers were reduced under pressure at 50° C. and diluted the residue with EtOAc (15 mL). Organic layer was washed with H2O (10 ml), brine (10 ml) and dried over Na2SO4; which was then concentrated under reduced pressure to give crude material (90 mg). Crude product was then purified by column chromatography [SiO2 (230-400 mesh), MeOH:DCM 0:95/5:95] to give the title compound (40 mg, 33.3%) as brown solid. MS: m/e=534.0 [M+H+].

Workup

  1. temperatureAfter cooling
  2. filtrationTLC shows formation of new spot, filtered the solid material by sintered funnel
  3. washwashed the solid residue by EtOAc (3×5 ml)
  4. customwere reduced under pressure at 50° C.
  5. additiondiluted the residue with EtOAc (15 mL)
  6. washOrganic layer was washed with H2O (10 ml), brine (10 ml)
  7. dry with materialdried over Na2SO4
  8. concentrationwhich was then concentrated under reduced pressure
  9. customto give crude material (90 mg)
  10. customCrude product was then purified by column chromatography [SiO2 (230-400 mesh), MeOH:DCM 0:95/5:95]

Sources & evidence

ORD record
ord-e710872ae793409a9d4f5bf6317eeb6e
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

Loading…