Hydrochloric Acid → {1-[2-(2-Chloro-benzylamino)-pyrido[4,3-d]pyrimidin-5-yl]-piperidin-4-yl}-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-methanone

HRID 41485Notes

Reaction equation

HRID 41485 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][NH:5][C:6]1[N:7]=[CH:8][C:9]2[C:15]([N:16]3[CH2:21][CH2:20][CH:19]([C:22]([OH:24])=O)[CH2:18][CH2:17]3)=[N:14][CH:13]=[CH:12][C:10]=2[N:11]=1.[N:29]1([CH2:35][CH2:36][OH:37])[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.CN1CCOCC1.OC1C2N=NNC=2C=CC=1.CN(C)CCCN=C=NCC.Cl>CN(C=O)C.O>[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][NH:5][C:6]1[N:7]=[CH:8][C:9]2[C:15]([N:16]3[CH2:17][CH2:18][CH:19]([C:22]([N:32]4[CH2:33][CH2:34][N:29]([CH2:35][CH2:36][OH:37])[CH2:30][CH2:31]4)=[O:24])[CH2:20][CH2:21]3)=[N:14][CH:13]=[CH:12][C:10]=2[N:11]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 76771-(2-Hydroxyethyl)piperazineHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 208551921-[2-(2-Chloro-benzylamino)-pyrido[4,3-d]pyrimidin-5-yl]-piperidine-4-carboxylic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 58450175{1-[2-(2-Chloro-benzylamino)-pyrido[4,3-d]pyrimidin-5-yl]-piperidin-4-yl}-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-methanoneYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-[2-(2-Chloro-benzylamino)-pyrido[4,3-d]pyrimidin-5-yl]-piperidine-4-carboxylic acid 14 (50 mg, 0.13 mmol), 2-piperazin-1-yl-ethanol (17.0 mg, 0.13 mmol) and 4-Methylmorpholine (70 μL, 0.64 mmol) were dissolved in DMF (3 mL). To this mixture hydroxybenzotriazole (17.0 mg, 0.13 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide×HCl (24.0 mg, 0.13 mmol) were added and the mixture was stirred for 48 h at room temperature. Water was added to the mixture and the precipitate formed was filtered off and dried in vacuo. The residue was purified by silica chromatography (ethyl acetate/cyclohexane) to yield in a colorless solid (27.8 mg, 0.05 mmol, 43%) characterized as 15.

Workup

  1. customthe precipitate formed
  2. filtrationwas filtered off
  3. customdried in vacuo
  4. customThe residue was purified by silica chromatography (ethyl acetate/cyclohexane)

Sources & evidence

ORD record
ord-07160a1e855a4eda8e8dc664de9f2c2e
Source dataset
uspto-grants-2013_09
Patent number
US08530650B2

Reaction notes

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