1,2-Dichloroethane → HCID 58014781, compound

HRID 1888934Notes

Reaction equation

HRID 1888934 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[C:21]([C:22]([OH:24])=O)=[CH:20][N:19]=[C:18](Cl)[N:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:26]1[CH:27]=[CH:28][C:29]2[N:34]([OH:35])[N:33]=[N:32][C:30]=2[CH:31]=1.C(Cl)CCl.[NH3:40]>CN(C=O)C.CCOC(C)=O.O>[N:34]1([O:35][C:18]2[N:17]=[C:16]([NH:15][CH2:14][CH:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:13][CH2:12]3)[C:21]([C:22](=[O:24])[NH2:40])=[CH:20][N:19]=2)[C:29]2[CH:28]=[CH:27][CH:26]=[CH:31][C:30]=2[N:32]=[N:33]1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 58014948HCID 58014948, compound

Product 1

HCID 58014781HCID 58014781, compoundYield 91.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-((1-(tert-butoxycarbonyl)piperidin-4-yl)methylamino)-2-chloropyrimidine-5-carboxylic acid (0.353 g, 0.953 mmol) and HOBt (0.219 g, 1.43 mmol) in DMF (5 mL), EDC (0.274 g, 1.43 mmol) was added. After being stirred for 1 h, NH3 (0.5 M in dioxane, 5.5 mL, 2.75 mmol) was added. The mixture was stirred for 20 h. Water and EtOAc were added. The organic phase was separated, washed with 1N HCl, then with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give tert-butyl 4-((2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-5-carbamoylpyrimidin-4-ylamino)methyl)piperidine-1-carboxylate as a solid (0.410 g).

Workup

  1. stirringThe mixture was stirred for 20 h
  2. customThe organic phase was separated
  3. washwashed with 1N HCl
  4. dry with materialwith 5% NaHCO3, dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b94a92b6318f4642bf0488228d09381f
Source dataset
uspto-grants-2013_08
Patent number
US08501944B2

Reaction notes

Loading…