Triethylamine → HCID 86675731, compound

HRID 2403231Notes

Reaction equation

HRID 2403231 reaction equation
[C@H:1]1([NH2:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH2:10])[CH:8]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[N:19]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:20]=[O:21]>CN(C=O)C>[NH2:10][C:7]1[CH:8]=[C:9]2[C:4]([CH2:3][CH2:2][C@H:1]2[NH:11][C:20](=[O:21])[NH:19][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76283Ethyl isocyanatoacetateHCID 50999334HCID 50999334, compound

Product 1

HCID 86675731HCID 86675731, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

(R)-2,3-dihydro-1H-indene-1,6-diamine (1 eq, 100 mg, 0.46 mmol) and triethylamine (2.5 eq, 158 μL, 1.15 mmol) were dissolved in 2 mL of DMF. The reaction mixture was cooled at 0° C. and ethyl isocyanatoacetate (1 eq, 59 mg, 51 μL, 0.46 mmol) was added dropwise and stirred for 2 hours at 0° C. The reaction mixture was concentrated and purified on reverse phase (H2O/MeCN) to afford the compound 46 (26 mg, 21%) as a white solid Rf=0.26. 1H NMR (300 MHz, DMSO): δ 6.91 (d, J=7.8, 1H), 6.47-6.39 (m, 2H), 6.36 (d, J=8.3 Hz, 1H), 6.11 (t, J=5.9 Hz, 1H), 5.02-4.88 (m, 3H), 4.13 (q, J=7.1 Hz, 2H), 3.83 (d, J=6.0, Hz 2H), 2.87-2.57 (m, 2H), 2.40-2.25 (m, 1H), 1.72. 1.56 (m, 1H), 1.31-1.17 (t, J=7.2 Hz, 3H). HPLC method A tr=5.60 nm (93.4%). ESI-MS m/z: 278.2 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified on reverse phase (H2O/MeCN)

Sources & evidence

ORD record
ord-8ccbab49dd564a33ac829fee96987b32
Source dataset
uspto-grants-2014_08
Patent number
US08802666B2

Reaction notes

Loading…