4-Hydroxybenzoic Acid → HCID 69300084, compound

HRID 131255Notes

Reaction equation

HRID 131255 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.Cl.Cl.[CH2:13]([O:15][C:16]1[CH:17]=[C:18]([CH:35]=[CH:36][CH:37]=1)[CH2:19][N:20]1[C:24]2=[N:25][CH:26]=[N:27][C:28]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)=[C:23]2[CH:22]=[N:21]1)[CH3:14].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C.C(Cl)Cl>[CH2:13]([O:15][C:16]1[CH:17]=[C:18]([CH:35]=[CH:36][CH:37]=1)[CH2:19][N:20]1[C:24]2=[N:25][CH:26]=[N:27][C:28]([N:29]3[CH2:30][CH2:31][N:32]([C:6](=[O:8])[C:5]4[CH:4]=[CH:3][C:2]([OH:1])=[CH:10][CH:9]=4)[CH2:33][CH2:34]3)=[C:23]2[CH:22]=[N:21]1)[CH3:14]

Participants

9

Reactant 5

HCID 1354-Hydroxybenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69298924HCID 69298924, compound

Product 1

HCID 69300084HCID 69300084, compoundYield 80.2%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To 4-hydroxybenzoic acid (1.06 g) is added successively methylene chloride (30 mL), 1-(3-ethoxybenzyl)-4-piperazin-1-yl-1H-pyrazolo[3,4-d]pyrimidine dihydrochloride (3.02 g), 1-hydroxybenzotriazole (1.25 g), triethylamine (3.7 mL) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.78 g). The mixture is stirred at room temperature for 17 hours. The reaction mixture is diluted with chloroform and thereto is added a saturated sodium hydrogencarbonate solution. After stirring, the organic layer is separated and evaporated to remove solvent. The resultant residue is purified by flash column chromatography on silica gel (Solvent; chloroform:methanol=50:1) to give 1-(3-ethoxybenzyl)-4-[4-(4-hydroxybenzoyl)piperazin-1-yl]-1H-pyrazolo[3,4-d]pyrimidine (2.70 g, yield; 80%) as an amorphous powder. MS (APCI) m/z: 459 [M+H]+

Workup

  1. stirringAfter stirring
  2. customthe organic layer is separated
  3. customevaporated
  4. customto remove solvent
  5. customThe resultant residue is purified by flash column chromatography on silica gel (Solvent; chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-3658a5b6ce384c74b347f9bffa7aaf18
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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