Water → HCID 86600596, compound

HRID 2113483Notes

Reaction equation

HRID 2113483 reaction equation
[CH2:1]([N:5]1[C:9]2[C:10](=[O:29])[N:11]([CH2:18][C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=3)[N:12]([CH2:15][C:16]#[N:17])[C:13](=[O:14])[C:8]=2[N:7]=[C:6]1Cl)[C:2]#[C:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].[C:37]([O:41][C:42]([NH:44][C@@H:45]1[CH2:50][CH2:49][CH2:48][NH:47][CH2:46]1)=[O:43])([CH3:40])([CH3:39])[CH3:38].O>CS(C)=O>[CH2:1]([N:5]1[C:9]2[C:10](=[O:29])[N:11]([CH2:18][C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=3)[N:12]([CH2:15][C:16]#[N:17])[C:13](=[O:14])[C:8]=2[N:7]=[C:6]1[N:47]1[CH2:48][CH2:49][CH2:50][C@@H:45]([NH:44][C:42]([O:41][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:43])[CH2:46]1)[C:2]#[C:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1514172(3R)-3-Aminopiperidine, 3-BOC protectedHCID 86600595HCID 86600595, compound

Product 1

HCID 86600596HCID 86600596, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 0.14 g 1-(but-2-ynyl)-2-chloro-5-cyanomethyl-6-(quinolin-2-ylmethyl)-5,6-dihydro-1H-imidazo[4,5-d]pyridazine-4,7-dione, 0.15 g potassium carbonate and 0.07 g (R)-3-tert-butoxycarbonylaminopiperidine in 2 ml dimethylsulphoxide is stirred for 5 h at 60° C. Then water is added and the mixture is extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulphate, and then the solvent is removed. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:1).

Workup

  1. extractionthe mixture is extracted three times with ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. customthe solvent is removed
  4. customThe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-0e3b723d4dbd4058863155f71a0e1845
Source dataset
uspto-grants-2008_10
Patent number
US07432262B2

Reaction notes

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