Isobutylamine → HCID 57545324, compound

HRID 2383120Notes

Reaction equation

C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([CH2:22][CH2:23][CH3:24])[C:20]([CH2:25][CH2:26][O:27][CH3:28])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)C1C=CC=CC=1.[CH2:29](N)[CH2:30][CH3:31].C([NH2:37])C(C)C.CO[CH2:40][CH2:41][C:42](Cl)=O.C(OC)(OC)(OC)CCC.FC1C=CC=CC=1.[CH3:62][S:63](C1C=CC(F)=CC=1)(=[O:65])=[O:64]>>[CH3:62][S:63]([C:30]1[CH:31]=[CH:42][C:41]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[C:13]4[N:21]([CH2:22][CH2:23][CH3:24])[C:20]([CH2:25][CH2:26][O:27][CH3:28])=[N:19][C:14]=4[C:15]([NH2:37])=[N:16][C:17]=3[CH:18]=2)=[CH:40][CH:29]=1)(=[O:65])=[O:64]

Participants

Reactant 7

HCID 6558Isobutylamine

HCID 7852Propylamine

HCID 10008Fluorobenzene

HCID 679941-Fluoro-4-(methylsulphonyl)benzene

HCID 1235121,1,1-Trimethoxybutane

HCID 27597283-Methoxypropanoyl chloride

HCID 67050950HCID 67050950, compound2×

Product 1

HCID 57545324HCID 57545324, compound

Procedure

The general methods described in Parts A-G of Example 1 were used to prepare 7-benzyloxy-2-(2-methoxyethyl)-1-propyl-1H-imidazo[4,5-c]quinoline. Propylamine was used in lieu of isobutylamine in Part E, and methoxypropionyl chloride was used in lieu of trimethyl orthobutyrate in Part G. 7-Benzyloxy-2-(2-methoxyethyl)-1-propyl-1H-imidazo[4,5-c]quinoline was treated according to the general methods described in Parts A-D of Examples 35-40. In Part B, the fluorobenzene used was 4-fluorophenyl methyl sulfone. Following chromatographic purification, the product was recrystallized from acetonitrile to provide 0.890 g of 7-(4-methanesulfonylphenoxy)-2-(2-methoxyethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine as dark tan needles, mp 210-212° C.

Workup

custompurification
customthe product was recrystallized from acetonitrile

Sources & evidence

ORD record: ord-0000943b55fb4f238b22a14c176b193d
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263594B2

Reaction notes

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