Ethanol → HCID 57722627, compound

HRID 1986866Notes

Reaction equation

HRID 1986866 reaction equation
C(OC([NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][NH:17][C:18]2[C:23]([C:24]([OH:26])=[O:25])=[CH:22][N:21]=[C:20]([NH:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])[N:19]=2)[CH2:12][CH2:11]1)=O)(C)(C)C.CCO.Cl.O1CCOCC1>C(Cl)(Cl)Cl>[NH2:8][CH2:9][CH:10]1[CH2:11][CH2:12][CH:13]([CH2:16][NH:17][C:18]2[C:23]([C:24]([OH:26])=[O:25])=[CH:22][N:21]=[C:20]([NH:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])[N:19]=2)[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 702EthanolHCID 204431481,4-Dioxane hydrochlorideHCID 57722671HCID 57722671, compound

Product 1

HCID 57722627HCID 57722627, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-{[4-(tert-butoxycarbonylamino-methyl)-cyclohexylmethyl]-amino}-2-(2-chloro-benzylamino)-pyrimidine-5-carboxylic acid (80 mg, 0.159 mmol) dissolved in 2:1 CHCl3:EtOH at room temperature was added 4.0 M HCl/dioxane (5.0 mL). The mixture was stirred at room temperature for 2 h then concentrated in vacuo to provide a crude white powder. The crude material was purified by preparative scale reverse phase HPLC using a 0.1% TFA-H2O/CH3CN mobile phase. The product-containing fractions were combined and concentrated in vacuo to provide 34 mg of the title compound as a white solid, 53%, m/z calculated for C20H26ClN5O2: 403.9, found: 404.4 (M+H)+.

Workup

  1. concentrationthen concentrated in vacuo
  2. customto provide a crude white powder
  3. customThe crude material was purified by preparative scale reverse phase HPLC
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4eaa7930d5994575aa3e08ee27da3a92
Source dataset
uspto-grants-2009_06
Patent number
US07550473B2

Reaction notes

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