Diisopropylethylamine → HCID 69298939, compound

HRID 131256Notes

Reaction equation

HRID 131256 reaction equation
Cl.Cl.[CH2:3]([O:5][C:6]1[CH:7]=[C:8]([CH:25]=[CH:26][CH:27]=1)[CH2:9][N:10]1[C:14]2=[N:15][CH:16]=[N:17][C:18]([N:19]3CCC[CH2:21][CH2:20]3)=[C:13]2[CH:12]=[N:11]1)[CH3:4].[CH:28]([N:31](CC)C(C)C)(C)[CH3:29].Cl[C:38]([O:40][C:41]1[CH:46]=[CH:45][C:44]([N+:47]([O-:49])=[O:48])=[CH:43][CH:42]=1)=[O:39].C(=O)([O-])O.[Na+]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:3]([O:5][C:6]1[CH:7]=[C:8]([CH:25]=[CH:26][CH:27]=1)[CH2:9][N:10]1[C:14]2=[N:15][CH:16]=[N:17][C:18]([N:19]3[CH2:29][CH2:28][N:31]([C:38]([O:40][C:41]4[CH:46]=[CH:45][C:44]([N+:47]([O-:49])=[O:48])=[CH:43][CH:42]=4)=[O:39])[CH2:21][CH2:20]3)=[C:13]2[CH:12]=[N:11]1)[CH3:4]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 516892Sodium BicarbonateHCID 131726915HCID 131726915, compound

Product 1

HCID 69298939HCID 69298939, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(3-ethoxybenzyl)-4-(1-piperadinyl)-1H-pyrazolo[3,4-d]pyrimidine dihydrochloride (60 mg) in methylene chloride (1.2 mL) is added N,N-diisopropylethylamine (85 μL) and 4-nitrophenyl chloroformate (49 mg) at 0° C., and the mixture is stirred at room temperature for 2.5 hours. The reaction mixture is diluted with chloroform (1 mL) and thereto is added a saturated sodium hydrogencarbonate solution (1.5 mL). After stirring, the organic layer is separated and the aqueous layer is extracted with chloroform. The organic layers are combined, dried over sodium sulfate, and filtered. The filtrate is concentrated and the residue is purified by column chromatography on silica gel (Solvent; n-hexane:ethyl acetate=9:1→0:10) to give 1-(3-ethoxybenzyl)-4-[4-[(4-nitrophenoxy)carbonyl]piperazin-1-yl]-1H-pyrazolo[3,4-d]pyrimidine (72 mg, yield; 100%) as an amorphous powder. MS (APCI) m/z; 504 [M+H]+

Workup

  1. stirringAfter stirring
  2. customthe organic layer is separated
  3. extractionthe aqueous layer is extracted with chloroform
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated
  7. customthe residue is purified by column chromatography on silica gel (Solvent; n-hexane:ethyl acetate=9:1→0:10)

Sources & evidence

ORD record
ord-f20fc27c78c645548c3e283d00d587d7
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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