Ethyl orthoformate → HCID 18783939, compound

HRID 1108637Notes

Reaction equation

[CH:1](OCC)(OCC)OCC.[NH2:11][C:12]1[C:13]([Cl:35])=[N:14][C:15]2[C:20]([C:21]=1[NH:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:19][CH:18]=[CH:17][CH:16]=2>>[C:31]([O:30][C:28]([NH:27][CH2:26][CH2:25][CH2:24][CH2:23][N:22]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[C:13]([Cl:35])[C:12]=2[N:11]=[CH:1]1)=[O:29])([CH3:32])([CH3:34])[CH3:33]

Participants

Reactant 2

HCID 31214Ethyl orthoformate

HCID 18783990HCID 18783990, compound

Product 1

HCID 18783939HCID 18783939, compoundYield 83.6%

Conditions

Temperature: 100 °C

Procedure

0.32 ml (1.92 mmol)of Triethyl ortho-formate was added to 0.14 g (0.384 mmol) of 3-amino-4-[4-(tert-butoxycarbonylamino)butylamino]-2-chloroquinoline. The mixture was heated at 100° C. and stirred overnight. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (chloroform:methanol=150:1 to 100:1 (v/v)) to obtain 0.12 g (0.321 mmol) of 1-[4-(tert-butoxycarbonylamino)butyl]-4-chloro-1H-imidazo[4,5-c]quinoline as pale orange powder (mp: 148-150° C.). ##STR43## Its spectroscopic data are as follows: IR (KBr) cm-1 : 1695, 1510.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe resulting residue was purified by silica gel column chromatography (chloroform:methanol=150:1 to 100:1 (v/v))

Sources & evidence

ORD record: ord-5d2c53c4634f40b2864e996ef57451da
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06069149

Reaction notes

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