Triethylamine → HCID 178484575, compound

HRID 630402Notes

Reaction equation

[OH:1][C:2]([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)([C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)[C:3]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([NH:12][CH3:13])[CH2:8][CH2:7]1)=[O:4].Br[CH2:25][CH2:26][OH:27].C(N(CC)CC)C.BrC(O)C>C(#N)C.C1COCC1>[OH:1][C:2]([C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)[C:3]([O:5][C@H:6]1[CH2:7][CH2:8][C@H:9]([N:12]([CH2:25][CH2:26][OH:27])[CH3:13])[CH2:10][CH2:11]1)=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of trans-4-(methylamino)cyclohexyl hydroxy(di-2-thienyl)acetate (intermediate 5; 300 mg; 0.85 mmol), 2-bromoethanol (0.145 ml; 2.05 mmol) and triethylamine (0.36 ml; 2.58 mmol) in 4.5 ml of acetonitrile and 3.5 ml of THF was stirred at 80° C. in a sealed vessel for 16 hr. Additional amounts of bromoethanol (0.145 ml; 2.05 mmol), triethylamine (0.36 ml; 2.58 mmol), acetonitrile (3.5 ml) and THF (3.5 ml) were added and the stirring and heating prosecuted for 24 additional hours. The solution was evaporated to dryness, dissolved in dichloromethane, washed with brine, dried and concentrated. Purification by preparative reversed-phase HPLC (Cl3CH/MeOH from 1:0 to 9:1) gave 76% of the title product as a colourless oil.

Workup

temperaturethe stirring and heating
customThe solution was evaporated to dryness
dissolutiondissolved in dichloromethane
washwashed with brine
customdried
concentrationconcentrated
customPurification by preparative reversed-phase HPLC (Cl3CH/MeOH from 1:0 to 9:1)

Sources & evidence

ORD record: ord-45f3946e87604b64b18545a6efa41cf4
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315463B2

Reaction notes

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