4-Nitrobenzoyl chloride → HCID 178525570, compound

HRID 1028756Notes

Reaction equation

HRID 1028756 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:27]3[CH2:30][CH:29]([CH2:31][OH:32])[CH2:28]3)=[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.[N+:33]([C:36]1[CH:44]=[CH:43][C:39]([C:40](Cl)=[O:41])=[CH:38][CH:37]=1)([O-:35])=[O:34].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[N+:33]([C:36]1[CH:37]=[CH:38][C:39]([C:40]([O:32][CH2:31][C@H:29]2[CH2:28][C@@H:27]([C:8]3[N:4]4[CH:5]=[CH:6][N:7]=[C:2]([Cl:1])[C:3]4=[C:10]([C:11]4[CH:20]=[C:19]5[C:14]([CH:15]=[CH:16][C:17]([C:21]6[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=6)=[N:18]5)=[CH:13][CH:12]=4)[N:9]=3)[CH2:30]2)=[O:41])=[CH:43][CH:44]=1)([O-:35])=[O:34]

Participants

5

Reactant 3

HCID 85024-Nitrobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 57681056{3-[8-Chloro-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclobutyl}methanol

Product 1

HCID 178525570HCID 178525570, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {3-[8-chloro-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclobutyl}methanol (46.52 g, 105.5 mmol) and 4-nitrobenzoyl chloride (23.55 g, 126.9 mmol) in methylene chloride (260 mL) was added N,N-diisopropylethyl amine (55.17 mL, 316.7 mmol). The mixture was stirred at rt for 15 h. Yellow precipitates were collected by filtration, washed with ethyl acetate, and dried to afford the title compound; 1H NMR (CDCl3, 400 MHz) δ 2.70-2.78 (m, 4H), 2.96-3.02 (m, 1H), 3.81-3.86 (m, 1H), 4.41 (d, J=4.8 Hz, 2H), 7.37 (d, J=5.2 Hz, 1H), 7.44-7.48 (m, 1H), 7.51-7.55 (m, 2H), 7.58 (d, J=5.2 Hz, 1H), 7.88-7.96 (m, 5H), 8.16-8.19 (m, 2H), 8.26-8.29 (m, 2H), 8.33 (d, J=8.8 Hz, 1H), 8.54 (s, 1H); MS (ES+): m/z 590 [MH+]; HPLC: tR=4.37 min (OpenLynx, polar—5 min).

Workup

  1. customYellow precipitates
  2. filtrationwere collected by filtration
  3. washwashed with ethyl acetate
  4. customdried

Sources & evidence

ORD record
ord-d0c5f9be45124ff8bfa290147cc6d528
Source dataset
uspto-grants-2014_05
Patent number
US08735405B2

Reaction notes

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