N-(2-aminoethyl)acetamide → HCID 20608709, compound

HRID 1990918Notes

Reaction equation

HRID 1990918 reaction equation
C(OC([N:8]1[C:12]2[N:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:15]=[C:16](Cl)[C:11]=2[CH:10]=[C:9]1[CH2:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=O)(C)(C)C.[C:32]([NH:35][CH2:36][CH2:37][NH2:38])(=[O:34])[CH3:33]>CS(C)=O>[O:25]([CH2:24][C:9]1[NH:8][C:12]2[N:13]=[C:14]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:15]=[C:16]([NH:38][CH2:37][CH2:36][NH:35][C:32](=[O:34])[CH3:33])[C:11]=2[CH:10]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 20608730HCID 20608730, compound

Product 1

HCID 20608709HCID 20608709, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A solution containing (8.1) (85 mg, 0.20 mmol), N-acetylethylene-diamine (201 mg, 1.95 mmol) and DMSO (3 mL) was heated to 100° C. After 1 h the temperature was raised to 130° C. After 3 h the reaction was cooled to room temperature and partitioned between EtOAc and water. The water layer was extracted with EtOAc (2×). The combined EtOAc layers are washed with water, dried over MgSO4, filtered and concentrated. Flash chromatography (SiO2; 1/10 EtOH/CHCl3, Rf 0.25) yielded 73 mg (93%) of a white foamy solid, mp. 196-197° C. 1H NMR (200 MHz, DMSO-d6): δ 1.79 (s, 3H), 3.36 (m, 2H), 3.61 (m, 2H), 5.12 (s, 2H), 6.59 (s, 1H), 6.89-7.09 (m, 3H), 7.20-7.50 (m, 5H), 7.57 (brt, 1H), 8.03 (brt, 1H), 8.39 (m, 2H), 11.81 (br s, 1H); MS (ES): 402.6 (MH+). tR (method A)=3.6 min.

Workup

  1. temperatureAfter 1 h the temperature was raised to 130° C
  2. temperatureAfter 3 h the reaction was cooled to room temperature
  3. custompartitioned between EtOAc and water
  4. extractionThe water layer was extracted with EtOAc (2×)
  5. washThe combined EtOAc layers are washed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4195a871a5ff4e0e9eef3fbab1bb008b
Source dataset
uspto-grants-2010_01
Patent number
US07645754B2

Reaction notes

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