Triethylamine → HCID 69300815, compound

HRID 131259Notes

Reaction equation

HRID 131259 reaction equation
Cl.[CH2:2]([O:4][C:5]1[CH:6]=[C:7]([CH:44]=[CH:45][CH:46]=1)[CH2:8][N:9]1[C:13]2=[N:14][CH:15]=[N:16][C:17]([N:18]3[CH2:23][CH2:22][N:21]([C:24](=[O:43])[C:25]4[CH:30]=[CH:29][C:28]([N:31]([C:37](=[O:42])[CH2:38][CH2:39][NH:40][CH3:41])[CH2:32][CH2:33][N:34]([CH3:36])[CH3:35])=[CH:27][CH:26]=4)[CH2:20][CH2:19]3)=[C:12]2[CH:11]=[N:10]1)[CH3:3].[Cl:47][C:48]([O:50][CH2:51][CH3:52])=[O:49].C(N(CC)CC)C>C(Cl)Cl.C(=O)([O-])O.[Na+]>[ClH:47].[CH2:2]([O:4][C:5]1[CH:6]=[C:7]([CH:44]=[CH:45][CH:46]=1)[CH2:8][N:9]1[C:13]2=[N:14][CH:15]=[N:16][C:17]([N:18]3[CH2:23][CH2:22][N:21]([C:24](=[O:43])[C:25]4[CH:26]=[CH:27][C:28]([N:31]([C:37](=[O:42])[CH2:38][CH2:39][N:40]([CH3:41])[C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH2:32][CH2:33][N:34]([CH3:36])[CH3:35])=[CH:29][CH:30]=4)[CH2:20][CH2:19]3)=[C:12]2[CH:11]=[N:10]1)[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 69299997HCID 69299997, compound

Product 1

HCID 69300815HCID 69300815, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of the compound obtained in Example 725 (50 mg) in methylene chloride (3 mL) is added ethyl chloroformate (10 μL) and triethylamine (22 μL) and the mixture is stirred at room temperature overnight. The reaction mixture is diluted with a saturated sodium hydrogencarbonate solution and the mixture is extracted with chloroform. The organic layer is evaporated to remove solvent and the residue is purified by column chromatography on silica gel (solvent; chloroform/methanol=10:1), and the resultant product is treated in the same manner as described in Example 4 (3) to give 1-(3-ethoxybenzyl)-4-[4-[4-[N-[3-[N-methyl-N-(ethoxycarbonyl)amino]-propionyl)-N-[2-(dimethylamino)ethyl]amino]benzoyl]piperazin-1-yl]-1H-pyrazolo-[3,4-d]pyrimidine hydrochloride (17 mg, yield; 30%) as an amorphous powder. MS (APCI) m/z: 686 [M+H]+

Workup

  1. extractionthe mixture is extracted with chloroform
  2. customThe organic layer is evaporated
  3. customto remove solvent
  4. customthe residue is purified by column chromatography on silica gel (solvent; chloroform/methanol=10:1)
  5. additionthe resultant product is treated in the same manner

Sources & evidence

ORD record
ord-eff5e6d039a34194abcdacea37bfc732
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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