Triethylamine → HCID 89666819, compound

HRID 2171239Notes

Reaction equation

HRID 2171239 reaction equation
[C:1](=[O:12])([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])OC(C)(C)C.C(N(CC)CC)C.[N+:20]([C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][N:27]=[C:26]2[NH2:32])([O-:22])=[O:21].[Cl-].[NH4+]>CN(C1C=CN=CC=1)C.C1COCC1>[N+:20]([C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][N:27]=[C:26]2[NH:32][C:1](=[O:12])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])([O-:22])=[O:21]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31366553-Amino-5-nitroindazoleHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 89666819HCID 89666819, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Di-tert-butyl carbonate (1.76 g), triethylamine (1.13 ml), and DMAP (10 mg) were added to a THF (8.2 ml) solution containing 5-nitro-1H-indazol-3-amine (1.45 g) under ice cooling, followed by stirring for 20 minutes. A saturated ammonium chloride aqueous solution was added to the reaction solution, followed by extraction with ethyl acetate. The organic layers were extracted with water and saturated saline and dried over sodium sulfate and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=1:0 to 3:2) and a yellow solid of tert-butyl (5-nitro-1H-indazol-3-yl)carbamate (1.8 g) was thus obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. extractionThe organic layers were extracted with water and saturated saline
  3. dry with materialdried over sodium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=1:0 to 3:2)

Sources & evidence

ORD record
ord-ba7c7df954f84b2da183219df764bc5d
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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