Isopropanol → HCID 18173110, compound

HRID 395878Notes

Reaction equation

HRID 395878 reaction equation
[O:1]=[C:2]1[CH2:8][CH:7]2[CH:9]([C:10](O)=O)[CH:4]([CH2:5][CH2:6]2)[CH2:3]1.Cl.[NH2:14][C:15]1[NH:20][C:19](=[O:21])[NH:18][C:17](=[O:22])[C:16]=1[NH2:23].CCN(C(C)C)[CH:27]([CH3:29])[CH3:28].[OH-].[K+].[CH3:35][CH:36](O)[CH3:37]>C(Cl)Cl.C(Cl)CCl>[O:1]=[C:2]1[CH2:3][CH:4]2[CH:9]([C:10]3[NH:23][C:16]4[C:17](=[O:22])[N:18]([CH2:28][CH2:27][CH3:29])[C:19](=[O:21])[N:20]([CH2:35][CH2:36][CH3:37])[C:15]=4[N:14]=3)[CH:7]([CH2:6][CH2:5]2)[CH2:8]1

Participants

8

Reactant 5

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 76725DiaminouracildihydrochlorideHCID 81531DiisopropylethylamineHCID 18173119HCID 18173119, compound

Product 1

HCID 18173110HCID 18173110, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

3-Oxo-bicyclo[3.2.1]octane-8-carboxylic acid (205 mg) from step 1 was coupled to diaminouracil HCl (395 mg) using EDC (287 mg) in CH2Cl2 in the presence of DIEA (490 mg) and cyclized in iPrOH (50 ml), 1N KOH (10 ml) at reflux overnight. The crude product was purified on silica column. Yield (210 mg). Mass (ES+ 359).

Workup

  1. customThe crude product was purified on silica column
  2. customYield (210 mg)

Sources & evidence

ORD record
ord-5a6264c1e95f470290a9c7bc483c64df
Source dataset
uspto-grants-2003_08
Patent number
US06605600B1

Reaction notes

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