Benzene, (3-bromopropoxy)- → 1-(2-methylcyclohexyl)-3-(3-phenoxypropyl)-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one

HRID 1696268Notes

Reaction equation

HRID 1696268 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[N:8]1[C:12]2=[C:13]3[CH:19]=[CH:18][NH:17][C:14]3=[N:15][CH:16]=[C:11]2[NH:10][C:9]1=[O:20].[C:21]1([O:27][CH2:28][CH2:29][CH2:30]Br)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.N12CNCC1=CCCC2>>[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[N:8]1[C:12]2=[C:13]3[CH:19]=[CH:18][NH:17][C:14]3=[N:15][CH:16]=[C:11]2[N:10]([CH2:30][CH2:29][CH2:28][O:27][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:9]1=[O:20]

Participants

4

Reactant 3

HCID 68522Benzene, (3-bromopropoxy)-HCID 141783371,2,3,5,6,7-Hexahydroimidazo[1,5-a]pyridineHCID 672781941-(2-methylcyclohexyl)-3,6-dihydroimidazo-[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one

Product 1

HCID 672782971-(2-methylcyclohexyl)-3-(3-phenoxypropyl)-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(2-methylcyclohexyl)-3,6-dihydroimidazo-[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (0.030M solution in N,N-dimethylformamide, 1.00 mL), 3-bromopropyl phenyl ether (12.9 mg), 1,8-diazabicyclo[4,3,0]non-5-ene (0.013 mL), was heated at 60° C. for 16 hours. The solvent was removed in vacuo and purification by preparative high performance liquid chromatography gave 1-(2-methylcyclohexyl)-3-(3-phenoxypropyl)-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (2.6 mg).

Workup

  1. customThe solvent was removed in vacuo and purification by preparative high performance liquid chromatography

Sources & evidence

ORD record
ord-33800192a02e4f0e9591f937dd776101
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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