Hydrochloric Acid → HCID 10225506, compound

HRID 1760359Notes

Reaction equation

[Na].C([O:4][C:5]([C:7]1([C:26](OCC)=[O:27])[CH2:11][CH2:10][CH2:9][N:8]1[C:12]1[CH:13]=[N:14][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=2)=[CH:16][CH:17]=1)=O)C.[NH2:31][C:32]([NH2:34])=[O:33].Cl.C([OH:38])C>>[Br:25][C:22]1[CH:21]=[CH:20][C:19]([O:18][C:15]2[N:14]=[CH:13][C:12]([N:8]3[C:7]4([C:5](=[O:4])[NH:34][C:32](=[O:33])[NH:31][C:26]4=[O:27])[CH2:11][CH2:10][C:9]3=[O:38])=[CH:17][CH:16]=2)=[CH:24][CH:23]=1

Participants

Reactant 5

HCID 313Hydrochloric Acid

HCID 702Ethanol

HCID 1176Urea

HCID 5360545Sodium

HCID 12133937HCID 12133937, compound

Product 1

HCID 10225506HCID 10225506, compound

Procedure

Sodium metal (29 mg, 1.26 mmol) was added to 1.3 mL of ethanol and stirred until homogeneous. of 1-[6-(4-Bromo-phenoxy)-pyridin-3-yl]-pyrrolidine-2,2-dicarboxylic acid diethyl ester (0.20 g, 0.42 mmol) was added, followed by urea (75 mg, 1.26 mmol) and the mixture was stirred for 5 minutes at 80° C. The mixture was cooled to ambient temperature, acidified with 1M hydrochloric acid and extracted 3× with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (3:1 hexane-ethyl acetate), affording 28 mg of 1-[6-(4-Bromo-phenoxy)-pyridin-3-yl]-1,7,9-triaza-spiro[4.5]decane-2,6,8,10-tetraone as a colorless solid. HPLC Ret. time: 2.201 min; MS (APCl, m/z): 436 [M−H]−; 438 [M+H]+.

Workup

stirringthe mixture was stirred for 5 minutes at 80° C
extractionextracted 3× with ethyl acetate
dry with materialThe combined organic phases were dried over sodium sulphate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography (3:1 hexane-ethyl acetate)

Sources & evidence

ORD record: ord-3bf8c8f1d2044563881c618b814a5284
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06841671B2

Reaction notes

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