1,2-Dichloroethane → HCID 58014797, compound

HRID 533448Notes

Reaction equation

HRID 533448 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH2:17][NH:18][C:19]2[C:24]([C:25](O)=[O:26])=[CH:23][N:22]=[C:21](Cl)[N:20]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:29]1[CH:34]=[C:33]2[N:35]=[N:36][N:37]([OH:38])[C:32]2=[CH:31][CH:30]=1.O.C(Cl)CCl.[NH3:44]>CN(C=O)C.CCOC(C)=O.O>[N:37]1([O:38][C:21]2[N:20]=[C:19]([NH:18][CH2:17][CH:13]3[CH2:14][CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:10])[CH2:12]3)[C:24]([C:25](=[O:26])[NH2:44])=[CH:23][N:22]=2)[C:32]2[CH:31]=[CH:30][CH:29]=[CH:34][C:33]=2[N:35]=[N:36]1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 27960291-Hydroxybenzotriazole hydrateHCID 58014721HCID 58014721, compound

Product 1

HCID 58014797HCID 58014797, compoundYield 84.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-((1-(benzyloxycarbonyl)piperidin-3-yl)methylamino)-2-chloropyrimidine-5-carboxylic acid (745 mg, 1.84 mmol) and HOBt monohydrate (422 mg, 2.76 mmol) in DMF (10 mL), EDC (529 mg, 2.76 mmol) was added. After 1 h of stirring, NH3 (0.5 M in dioxane, 11.0 mL, 5.50 mmol) was added. The mixture was stirred at room temperature for 18 h. Water and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give benzyl 3-((2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-5-carbamoylpyrimidin-4-ylamino)methyl)piperidine-1-carboxylate (779 mg).

Workup

  1. stirringThe mixture was stirred at room temperature for 18 h
  2. customThe organic phase was separated
  3. washwashed with 5% NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a20a028905b40efae01572bd26cbb46
Source dataset
uspto-grants-2014_10
Patent number
US08853230B2

Reaction notes

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