N-[(3-Chloro-pyrazin-2-yl)-(2-phenyl-quinolin-7-yl)-methyl]-acetamide → 7-(8-Chloro-3-methyl-imidazo[1,5-a]pyrazin-1-yl)-2-phenyl-quinoline

HRID 493749Notes

Reaction equation

[Cl:1][C:2]1[C:3]([CH:8]([C:13]2[CH:22]=[C:21]3[C:16]([CH:17]=[CH:18][C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[N:20]3)=[CH:15][CH:14]=2)[NH:9][C:10](=O)[CH3:11])=[N:4][CH:5]=[CH:6][N:7]=1>O=P(Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]2[N:4]([C:10]([CH3:11])=[N:9][C:8]=2[C:13]2[CH:22]=[C:21]3[C:16]([CH:17]=[CH:18][C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[N:20]3)=[CH:15][CH:14]=2)[CH:5]=[CH:6][N:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

N-[(3-Chloro-pyrazin-2-yl)-(2-phenyl-quinolin-7-yl)-methyl]-acetamide (273.0 mg, 0.702 mmol) was dissolved in 20 mL of POCl3. The reaction was heated to 80° C. for 24 h. The excess POCl3 was removed in vacuo. The residue was worked up by basifying with cold 2.0 M NH3 in IPA followed by the addition of CH2Cl2 and water. The aqueous layer was washed with CH2Cl2 (2×). The organic layers where combined, dried over sodium sulfate, filtered and concentrated in vacuo to yield a light brown oil; 1H NMR (400 MHz, CDCl3) δ 2.77 (s, 3H), 7.41-7.59 (m, 4H), 7.70-7.72 (m, 1H), 7.88-7.93 (m, 3H), 8.19-8.28 (brm, 3H), 8.55 (brs, 1H); MS (ES+): 370.96 (M+1), 372.97 (M+3), 373.98 (M+4).

Workup

customThe excess POCl3 was removed in vacuo
additionfollowed by the addition of CH2Cl2 and water
washThe aqueous layer was washed with CH2Cl2 (2×)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customto yield a light brown oil

Sources & evidence

ORD record: ord-80d7131466a5430c92e5fc641ed67281
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07534797B2

Reaction notes

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