Trifluoroacetic acid → HCID 66691911, compound

HRID 1808881Notes

Reaction equation

HRID 1808881 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:15]([O-:17])=[O:16])[C:5]([NH2:14])=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.C(O)(C(F)(F)F)=O.CCN(C(C)C)C(C)C.[CH3:34][O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[C:42]1[C:46]([C:47](O)=[O:48])=[C:45]([CH3:50])[O:44][N:43]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH2:14][C:5]1[N:6]=[C:7]([N:8]2[CH2:9][CH2:10][N:11]([C:47]([C:46]3[C:42]([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=4[O:35][CH3:34])=[N:43][O:44][C:45]=3[CH3:50])=[O:48])[CH2:12][CH2:13]2)[C:2]([Cl:1])=[CH:3][C:4]=1[N+:15]([O-:17])=[O:16]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 64841003-(2-Methoxyphenyl)-5-methyl-1,2-oxazole-4-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66692536HCID 66692536, compound

Product 1

HCID 66691911HCID 66691911, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-3-nitro-6-(piperazin-1-yl)pyridin-2-amine, TFA (0.192 mmol) in DMF (2 ml) was added DIEA (0.134 ml, 0.768 mmol), 3-(2-methoxyphenyl)-5-methylisoxazole-4-carboxylic acid (44.8 mg, 0.192 mmol) and HATU (73.0 mg, 0.192 mmol). The reaction was stirred at room temperature for 1 h. The reaction mixture was purified by preparative HPLC to afford 69 mg (73.7% for 3 steps) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 8.25 (1H, s), 7.58 (1H, dd, J=7.5, 1.7 Hz), 7.52-7.39 (1H, m), 7.08-7.06 (1H, m), 6.97 (1H, d, J=7.9 Hz), 3.79 (3 H, s), 3.72 (2H, br. s.), 3.55 (2H, br. s.), 3.16 (2H, br. s.), 2.98 (2H, br. s.), 2.55 (3H, s).

Workup

  1. customThe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-598cc207b5e340e4988a9e1bf098100c
Source dataset
uspto-grants-2013_01
Patent number
US08362004B2

Reaction notes

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