Hydrochloric Acid → HCID 57897283, compound

HRID 416880Notes

Reaction equation

HRID 416880 reaction equation
NC1C([N+]([O-])=O)=C(N2CCN(CC(NC3SC=CN=3)=O)CC2)C(Br)=CN=1.Cl[C:28]1[C:33]([Cl:34])=[CH:32][N:31]=[C:30]([NH2:35])[C:29]=1[N+:36]([O-:38])=[O:37].CCN(C(C)C)C(C)C.[N:48]1[CH:53]=[CH:52][C:51]([CH:54]([N:56]2[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]2)[CH3:55])=[CH:50][CH:49]=1.Cl>CC(O)C>[Cl:34][C:33]1[C:28]([N:59]2[CH2:60][CH2:61][N:56]([CH:54]([C:51]3[CH:50]=[CH:49][N:48]=[CH:53][CH:52]=3)[CH3:55])[CH2:57][CH2:58]2)=[C:29]([N+:36]([O-:38])=[O:37])[C:30]([NH2:35])=[N:31][CH:32]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 3614708HCID 3614708, compoundHCID 468676602-Amino-4,5-dichloro-3-nitropyridineHCID 468678032-(4-(2-amino-5-bromo-3-nitropyridin-4-yl)piperazin-1-yl)-N-(thiazol-2-yl)acetamide

Product 1

HCID 57897283HCID 57897283, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

This was prepared using the same procedure as for 2-(4-(2-amino-5-bromo-3-nitropyridin-4-yl)piperazin-1-yl)-N-(thiazol-2-yl)acetamide, but here using 4,5-dichloro-3-nitropyridin-2-amine (22 mg, 0.106 mmol), iPrOH (1 mL), DIPEA (0.2 mL) and 1-(1-(pyridin-4-yl)ethyl)piperazine.3×HCl (1.1 eq, 0.116 mmol, 35 mg). Filtration and washing as previously described gave the product (28 mg, 73%) as a yellow solid; δH (500 MHz, DMSO-d6) 1.30 (d, J=6.7 Hz, 3H, CHCH3), 2.42 (s, br, 2H, piperazine NCH2), 2.53 (s, br, 2H, piperazine NCH2), 3.05 (s, br, 4H, piperazine N(CH2)2), 3.54 (q, J=6.8 Hz, 1H, CHCH3), 6.94 (s, br, 2H, NH2), 7.34 (d, J=6.0 Hz, 2H, pyridine H-2 & H-6), 8.04 (s, 1H, chloropyridine H-6), 8.51 (d, J=6.0 Hz, 2H, pyridine H-3 & H-5);

Workup

  1. customThis was prepared
  2. filtrationFiltration
  3. washwashing

Sources & evidence

ORD record
ord-270f98d710454cc3a53add8be2d85a33
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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