Diisopropylethylamine → HCID 57897235, compound

HRID 416732Notes

Reaction equation

[Br:1][C:2]1[C:3](Cl)=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([NH2:8])=[N:6][CH:7]=1.[N:13]1([CH2:19][C:20]([N:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)=[O:21])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(N(C(C)C)CC)(C)C>C(O)(C)C>[NH2:8][C:5]1[C:4]([N+:9]([O-:11])=[O:10])=[C:3]([N:16]2[CH2:15][CH2:14][N:13]([CH2:19][C:20]([N:22]3[CH2:23][CH2:24][CH2:25][CH2:26]3)=[O:21])[CH2:18][CH2:17]2)[C:2]([Br:1])=[CH:7][N:6]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a mixture of 5-bromo-4-chloro-3-nitro-pyridin-2-ylamine (0.126 g, 0.50 mmol) and isopropanol (9 ml) was added 2-(piperazin-1-yl)-1-(pyrrolidin-1-yl)ethanone (0.108 g, 0.55 mmol) followed by diisopropylethylamine (0.10 ml, 0.55 mmol). The reaction mixture was heated at 45° C. for 22 h, then allowed to cool to room temperature and the solvents were removed in vacuo. The residue was absorbed on silica gel and the free running powder was placed on a 10 g isolute silica column which was eluted with 70% ethyl acetate in dichloromethane and then 90% ethyl acetate in dichloromethane. The title compound was obtained as a yellow solid (0.162 g, 78%); 1H-NMR (500 MHz, DMSO-d6) 1.74 (m, 2H) and 1.85 (m, 2H) (pyrrolidine 3-CH2 and 4-CH2), 2.60 (br s, 4H, piperazine N(CH2)2), 3.04 (br s, 4H, piperazine N(CH2)2), 3.16 (s, 2H, NCH2CO), 3.27 (t, J=6.90 Hz, 2H) and 3.45 (t, J=6.70 Hz, 2H) (pyrrolidine 2-CH2 and 5-CH2), 7.02 (s, 2H, NH2), 8.16 (s, 1H, 6-H);

Workup

temperatureto cool to room temperature
customthe solvents were removed in vacuo
customThe residue was absorbed on silica gel
washwas eluted with 70% ethyl acetate in dichloromethane

Sources & evidence

ORD record: ord-63f3f6bbfe6146a38c3e5854b49d4439
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088761B2

Reaction notes

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