Diisopropylethylamine → HCID 178461368, compound

HRID 1353415Notes

Reaction equation

HRID 1353415 reaction equation
[CH3:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH2:8])[CH2:4][CH2:3]1.C[C@@H]1CC[C@H](N)CC1.Cl[C:18](OC1C=CC([N+]([O-])=O)=CC=1)=[O:19].C(N(C(C)C)CC)(C)C.[Cl:39][C:40]1[CH:49]=[C:48]2[C:43]([C:44]([N:50]3[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]3)=[CH:45][CH:46]=[N:47]2)=[CH:42][CH:41]=1>C(Cl)Cl.CO>[Cl:39][C:40]1[CH:49]=[C:48]2[C:43]([C:44]([N:50]3[CH2:55][CH2:54][N:53]([C:18]([NH:8][C@H:5]4[CH2:6][CH2:7][C@H:2]([CH3:1])[CH2:3][CH2:4]4)=[O:19])[CH2:52][CH2:51]3)=[CH:45][CH:46]=[N:47]2)=[CH:42][CH:41]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 7383897-Chloro-4-(piperazin-1-yl)quinolineHCID 178461304HCID 178461304, compoundHCID 178461305HCID 178461305, compound

Product 1

HCID 178461368HCID 178461368, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

As described for example 78, trans-4-methyl-1-cyclohexanamine (170 mg, 1.5 mmol) prepared in a similar manner as for cis-4-methyl-1-cyclohexanamine, 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 0.9 (d, 3H), 1.0–1.2 (m, 3H), 1.23–1.4 (m, 2H), 1.7 (m, 2H), 2.02 (m, 2H), 3.2 (m, 4H), 3.61 (m, 4H), 4.38 (m, 1H), 6.83 (d, 1H), 7.43 (d, 1H), 7.94 (d, 1H), 8.05 (s, 1H), 8.77 (d, 1H).

Workup

  1. customare reacted

Sources & evidence

ORD record
ord-44b3a22d6304494d9334d7f95c19d491
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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