1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 9804977, compound

HRID 1637199Notes

Reaction equation

N12CCCN=C1CCCCC2.Cl[C:13]1[C:14]2[CH:26]=[CH:25][C:24]([CH2:27][N:28]3[C:32]4[CH:33]=[N:34][CH:35]=[CH:36][C:31]=4[N:30]=[CH:29]3)=[CH:23][C:15]=2[S:16][C:17]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].[CH3:37][O:38][C:39]1[CH:40]=[C:41]([SH:45])[CH:42]=[CH:43][CH:44]=1>CN(C)C=O.O1CCCC1>[N:30]1[C:31]2[CH:36]=[CH:35][N:34]=[CH:33][C:32]=2[N:28]([CH2:27][C:24]2[CH:25]=[CH:26][C:14]3[C:13]([S:45][C:41]4[CH:42]=[CH:43][CH:44]=[C:39]([O:38][CH3:37])[CH:40]=4)=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[S:16][C:15]=3[CH:23]=2)[CH:29]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU--0.07 ml, 0.48 mmol) was added to a mixture of ethyl 3-(chloro)-6-(3H-imidazo[4,5-c]pyridin-3-ylmethyl)benzo[b]thiophene-2 carboxylate (Preparation 12, 150 mg, 0.4 mmol) and 3-methoxybenzenethiol (0.07 ml, 0.6 mmol) in a mixture of dimethylformamide (1 ml) and tetrahydrofuran (1 ml) under a nitrogen atmosphere. The solution was heated to 60° C. for 6 hours and then partitioned between ethyl acetate and water. The organics were separated and washed with water, dried (magnesium sulfate) and evaporated under reduced pressure. The residue was triturated with diethyl ether and hexane mixture to give the title compound as a colourless solid (155 mg).

Workup

custompartitioned between ethyl acetate and water
customThe organics were separated
washwashed with water
dry with materialdried (magnesium sulfate)
customevaporated under reduced pressure
customThe residue was triturated with diethyl ether and hexane mixture

Sources & evidence

ORD record: ord-04a30eaf5ec94f53965b9fe962b030cb
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06040309

Reaction notes

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