Hydrochloric Acid → HCID 59367574, compound

HRID 2079799Notes

Reaction equation

HRID 2079799 reaction equation
C(OC([O:8][NH:9][C:10]([C:12]1[CH:13]=[N:14][C:15]([N:18]2[CH2:23][CH:22]3[CH:20]([CH:21]3[N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH2:19]2)=[N:16][CH:17]=1)=[O:11])C)C(C)C.Cl.O1CCOCC1>C(Cl)Cl>[OH:8][NH:9][C:10]([C:12]1[CH:13]=[N:14][C:15]([N:18]2[CH2:23][CH:22]3[CH:20]([CH:21]3[N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[CH2:19]2)=[N:16][CH:17]=1)=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59367659HCID 59367659, compound

Product 1

HCID 59367574HCID 59367574, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(1-Isobutoxyethoxy) 2-(6-morpholin-4-yl-3-aza-bicyclo[3.1.0]hex-3-yl)pyrimidine-5-carboxamide (10 mg, 0.02 mmol) was dissolved in DCM (2 ml) and treated with 4M HCl in dioxane (0.4 ml, 0.1 mmol). The resultant mixture was stirred at r.t. for 30 min, then evaporated under reduced pressure and azeotroped with MeOH (3×5 ml) to give the title compound as a white solid (2.3 mg, 40%). LCMS purity 90%, m/z 306 [M+H]+, 1H NMR (300 MHz, CD3OD) δ: 2.49 (2H, br s), 2.85 (1H, br s), 3.55-3.87 (8H, m), 4.10 (4H, m), 8.72 (2H, s).

Workup

  1. customevaporated under reduced pressure
  2. customazeotroped with MeOH (3×5 ml)

Sources & evidence

ORD record
ord-93e2a5859f5243d4a03548188cbd7786
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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