Ammonium Chloride → HCID 22025333, compound

HRID 1792839Notes

Reaction equation

HRID 1792839 reaction equation
[C:1]1([C:7](=[N:14][CH2:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:17])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:39]1([S:45]([N:48]2[C:56]3[C:51](=[C:52]([CH2:60]Br)[CH:53]=[C:54]([Cl:59])[C:55]=3[O:57][CH3:58])[CH:50]=[N:49]2)(=[O:47])=[O:46])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.[NH4+].[Cl-]>C1COCC1>[C:39]1([S:45]([N:48]2[C:56]3[C:51](=[C:52]([CH2:60][CH:15]([N:14]=[C:7]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:17])[CH:53]=[C:54]([Cl:59])[C:55]=3[O:57][CH3:58])[CH:50]=[N:49]2)(=[O:47])=[O:46])[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 22025334HCID 22025334, compoundHCID 22025348HCID 22025348, compound

Product 1

HCID 22025333HCID 22025333, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

2-(Diphenylmethylenamino)-N-(4-phenyl-butyl)-acetamide (7) (0.57 g, 1.5 mmol) is dissolved in dry THF (5 mL) and cooled to −78° C. A solution of KHMDS (0.5 M in PhMe, 3.0 mL, 1.5 mmol) is added slowly to the imide. The solution is warmed to 0° C. and then cooled to −78° C. A solution of 1-benzenesulfonyl-4-bromomethyl-6-chloro-7-methoxy-1H-indazole (0.57 g, 1.4 mmol) in dry THF (4 mL) is added slowly at −78° C. and the solution is allowed to stir 15 min. The reactio is then poured into a solution of aqueous NH4Cl and extracted with EtOAc. The organic phase is washed with water, brine, dried over MgSO4 and concentrated. The crude reaction is purified by column chromatography (silica, 10–20% EtOAc/PhMe) to provide 3-(1-benzenesulfonyl-6-chloro-7-methoxy-1H-indazol-4-yl)-2-(diphenylmethylenamino)-N-(4-phenyl-butyl)-propionamide.

Workup

  1. temperatureThe solution is warmed to 0° C.
  2. temperaturecooled to −78° C
  3. extractionextracted with EtOAc
  4. washThe organic phase is washed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe crude reaction
  8. customis purified by column chromatography (silica, 10–20% EtOAc/PhMe)

Sources & evidence

ORD record
ord-2fcc050a462145c7bb42d8662cfb0bda
Source dataset
uspto-grants-2006_07
Patent number
US07078425B2

Reaction notes

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