Hydrochloric Acid → HCID 15521771, compound

HRID 1838219Notes

Reaction equation

C(=O)(O)[O-].[Na+].Br[CH2:7][CH2:8][CH2:9][CH2:10]Br.[NH2:12][C:13]1[CH:38]=[CH:37][C:16]([CH2:17][N:18]2[C:26]3[C:21](=[CH:22][C:23]([Cl:27])=[CH:24][CH:25]=3)[C:20]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])([CH3:28])[C:19]2=[O:36])=[C:15]([O:39][CH3:40])[CH:14]=1.Cl>CN(C)P(N(C)C)(N(C)C)=O.C(OCC)C>[Cl:27][C:23]1[CH:22]=[C:21]2[C:26](=[CH:25][CH:24]=1)[N:18]([CH2:17][C:16]1[CH:37]=[CH:38][C:13]([N:12]3[CH2:10][CH2:9][CH2:8][CH2:7]3)=[CH:14][C:15]=1[O:39][CH3:40])[C:19](=[O:36])[C:20]2([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[Cl:35])[CH3:28]

Participants

Conditions

Temperature: 115 °C

Procedure

0.4 g of sodium bicarbonate powder and 0.14 ml of 1,4-dibromobutane are added to 0.5 g of the compound of Example 48 in 50 ml of hexamethyl-phosphoramide. The reaction mixture is heated at 115° C. for 10 hours. The reaction mixture is hydrolysed at room temperature and extracted with ethyl acetate. The organic phase is washed several times with water and dried over anhydrous sodium sulphate and then the solvents are evaporated under reduced pressure. The residue obtained is purified by chromatography on a column of silica gel, elution being carried out with a 95/5 (v/v) cyclohexane/ethyl acetate mixture. The oil obtained is treated with hydrochloric acid in diethyl ether; M.p.=198° C. (HCl.0.4H2O).

Workup

customis hydrolysed at room temperature
extractionextracted with ethyl acetate
washThe organic phase is washed several times with water
dry with materialdried over anhydrous sodium sulphate
customthe solvents are evaporated under reduced pressure
customThe residue obtained
customis purified by chromatography on a column of silica gel, elution
customThe oil obtained

Sources & evidence

ORD record: ord-18b64a97df20492bad5c0b5679be6022
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06673790B1

Reaction notes

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