Diisopropylethylamine → HCID 136038646, compound

HRID 1992416Notes

Reaction equation

HRID 1992416 reaction equation
[Cl:1][C:2]1[C:3]([CH:8]([NH2:25])[C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][C:15]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[N:16]3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][N:7]=1.CCN(C(C)C)C(C)C.Cl[C:36](OC1C=CC([N+]([O-])=O)=CC=1)=[O:37]>C1COCC1>[Cl:1][C:2]1[C:3]2[N:4]([C:36](=[O:37])[NH:25][C:8]=2[C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][C:15]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[N:16]3)=[CH:11][CH:10]=2)[CH:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 51051365(3-Chloropyrazin-2-yl)(2-phenylquinolin-7-yl)methanamine

Product 1

HCID 136038646HCID 136038646, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

C-(3-Chloro-pyrazin-2-yl)-C-(2-phenyl-quinolin-7-yl)-methylamine (2.0 g, 5.8 mmol) was dissolved in anhydrous THF (35.0 mL), followed by the addition of DIPEA (1.21 mL, 6.92 mmol) at rt. The dark brown solution was then charged with para-nitrophenyl chloroformate (1.28 g, 6.34 mmol) at rt, and warmed to 45° C. for 17 h. The crude reaction was concentrated in vacuo and dissolved with EtOAc and water. Yellow precipitate crashed out of solution and was filtered. The solid was washed with hexanes and dried under vacuum to yield the title compound as a yellow solid; MS (ES+): m/z 373.04 (100) [MH+], 375.00 (30) [MH+++]; HPLC: tR=3.15 min (OpenLynx, polar—5 min); 1HNMR (400 MHz, DMSO-d6) δ ppm 6.80-7.05 (m, 2H), 7.43-7.66 (m, 4H), 7.79 (dd, J=8.34, 1.77 Hz, 1H), 8.02-8.17 (m, 2H), 8.19-8.35 (m, 4H), 8.53 (d, J=8.59 Hz, 1H).

Workup

  1. customThe crude reaction
  2. concentrationwas concentrated in vacuo
  3. dissolutiondissolved with EtOAc and water
  4. filtrationwas filtered
  5. washThe solid was washed with hexanes
  6. customdried under vacuum

Sources & evidence

ORD record
ord-ebf4bdcf923d40ecb379301d4542a293
Source dataset
uspto-grants-2010_01
Patent number
US07648987B2

Reaction notes

Loading…