Diisopropylethylamine → HCID 178461367, compound

HRID 1353414Notes

Reaction equation

HRID 1353414 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([NH2:8])[CH2:4][CH2:3]1.Cl[C:10](OC1C=CC([N+]([O-])=O)=CC=1)=[O:11].C(N(C(C)C)CC)(C)C.[Cl:31][C:32]1[CH:41]=[C:40]2[C:35]([C:36]([N:42]3[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]3)=[CH:37][CH:38]=[N:39]2)=[CH:34][CH:33]=1>C(Cl)Cl.CO>[Cl:31][C:32]1[CH:41]=[C:40]2[C:35]([C:36]([N:42]3[CH2:47][CH2:46][N:45]([C:10]([NH:8][C@H:5]4[CH2:6][CH2:7][C@@H:2]([CH3:1])[CH2:3][CH2:4]4)=[O:11])[CH2:44][CH2:43]3)=[CH:37][CH:38]=[N:39]2)=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 7383897-Chloro-4-(piperazin-1-yl)quinolineHCID 178461304HCID 178461304, compound

Product 1

HCID 178461367HCID 178461367, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

As described for example 78, cis-4-methyl-1-cyclohexanamine (170 mg, 1.5 mmol), 4-nitrophenyl chloroformate (302 mg, 1.5 mmol), diisopropyl(ethyl)amine (258 mg, 2 mmol), and 7-chloro-4-(piperazin-1-yl)quinoline (248 mg, 1 mmol) are reacted affording the title product after flash chromatography with CH2Cl2-MeOH. 1H NMR (DSMO-d6) δ 0.92 (d, 3H), 1.2 (m, 2H), 1.55–1.7 (m, 8H), 3.22 (m, 4H), 3.65 (m, 4H), 4.02 (br. s, 1H), 4.6 (m, 1H), 6.82 (d, 1H), 7.44 (d, 1H), 7.98 (d, 1H), 8.06 (s, 1), 8.78 (d, 1H).

Workup

  1. customare reacted

Sources & evidence

ORD record
ord-e497f6e5375448eca9f04b124405c8cf
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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