Water → HCID 86600596, compound

HRID 746384Notes

Reaction equation

HRID 746384 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-15978c47957c464ea36131eb8a8342cc
Source dataset
uspto-grants-2008_07
Patent number
US07393847B2

Reaction notes

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