Ammonia → HCID 16755039, compound

HRID 1992414Notes

Reaction equation

HRID 1992414 reaction equation
Cl[C:2]1[C:3]2[N:4]([C:8]([O:27][CH2:28][CH3:29])=[N:9][C:10]=2[C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:18]3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.C(O)(C)C.[NH3:34]>>[CH2:28]([O:27][C:8]1[N:4]2[CH:5]=[CH:6][N:7]=[C:2]([NH2:34])[C:3]2=[C:10]([C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)=[N:18]3)=[CH:13][CH:12]=2)[N:9]=1)[CH3:29]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 3776IsopropanolHCID 58902026HCID 58902026, compound

Product 1

HCID 16755039HCID 16755039, compound

Conditions

Temperature
-20 °C

Procedure

7-(8-Chloro-3-ethoxy-imidazo[1,5-a]pyrazin-1-yl)-2-phenyl-quinoline (20.0 mg, 0.050 mmol) was dissolved into a 80 mL sealed tube with isopropyl alcohol (1.0 mL, 3.0 mmol). The solution was cooled to −20° C. and charged with ammonia gas. The reaction was heated to 110 IC for 72 hours. The reaction was then cooled, concentrated in vacuo and dissolved with CH2Cl2. The crude product was purified via silica gel column chromatography, (Jones, 2.0 gram column; 100% EtOAc) to yield the title compound as a yellow solid; MS (ES+): m/z 382.08 (90) [MH+], 383.09 (30) [MH++]. HPLC: tR=2.26 min (OpenLynx, polar—5 min); 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.52 (t, J=7.07 Hz, 3H), 4.66 (q, J=7.07 Hz, 2H), 6.96 (d, J=5.05 Hz, 1H), 7.13 (d, J=5.05 Hz, 1H), 7.34-7.63 (m, 3H), 7.75-8.01 (m, 3H), 8.10-8.32 (m, 3H), 8.40 (s, 1H).

Workup

  1. temperatureThe reaction was heated to 110 IC for 72 hours
  2. temperatureThe reaction was then cooled
  3. concentrationconcentrated in vacuo
  4. dissolutiondissolved with CH2Cl2
  5. customThe crude product was purified via silica gel column chromatography, (Jones, 2.0 gram column; 100% EtOAc)

Sources & evidence

ORD record
ord-d35f2f25bc1e4809b13ca6b30bba8c82
Source dataset
uspto-grants-2010_01
Patent number
US07648987B2

Reaction notes

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