Diisopropylethylamine → HCID 58418305, compound

HRID 588496Notes

Reaction equation

HRID 588496 reaction equation
Cl.[NH2:2][CH:3]([C:5]1[S:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:6]=1)[CH3:4].C(N(CC)C(C)C)(C)C.[N:23]([CH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1)=[C:24]=[O:25]>ClCCCl>[CH:26]1([NH:23][C:24](=[O:25])[NH:2][CH:3]([C:5]2[S:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:6]=2)[CH3:4])[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 643500Cyclopentyl IsocyanateHCID 67395898HCID 67395898, compound

Product 1

HCID 58418305HCID 58418305, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution of methyl 5-(1-aminoethyl)thiophene-2-carboxylate hydrochloride (33.2 mg, 0.150 mmol) and N,N-diisopropylethylamine (104 μL, 0.60 mmol) dissolved in 1,2-dichloroethane (1 mL) was added isocyanatocyclopentane (24 mg, 0.22 mmol). The reaction solution was shaken at room temperature overnight. The solution was further diluted with DCE (2 mL) and washed with saturated aqueous NaHCO3 (2 mL). The layers were separated and the organic layer concentrated to afford methyl 5-(1-(3-cyclopentylureido)ethyl)thiophene-2-carboxylate as an oil residue. LC-MS: (FA) ES+ 297.

Workup

  1. washwashed with saturated aqueous NaHCO3 (2 mL)
  2. customThe layers were separated
  3. concentrationthe organic layer concentrated

Sources & evidence

ORD record
ord-3fad1151c9a34d2fa3368c912ad02420
Source dataset
uspto-grants-2016_01
Patent number
US09227951B2

Reaction notes

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