Trifluoroacetic acid → HCID 68227418, compound

HRID 1808888Notes

Reaction equation

HRID 1808888 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:6][C:5]([NH:14][C:15](=[O:25])[C:16]2[CH:21]=[CH:20][C:19]([N:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=2)=[C:4]([N+:26]([O-:28])=[O:27])[CH:3]=1.C(O)(C(F)(F)F)=O.[CH3:36][O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[C:44]1[C:48]([C:49](O)=[O:50])=[C:47]([CH3:52])[NH:46][N:45]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([C:49]([C:48]3[C:44]([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=4[O:37][CH3:36])=[N:45][NH:46][C:47]=3[CH3:52])=[O:50])[CH2:10][CH2:9]2)=[CH:6][C:5]([NH:14][C:15](=[O:25])[C:16]2[CH:17]=[CH:18][C:19]([N:22]([CH3:23])[CH3:24])=[CH:20][CH:21]=2)=[C:4]([N+:26]([O-:28])=[O:27])[CH:3]=1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 54851625HCID 54851625, compoundHCID 66692213HCID 66692213, compound

Product 1

HCID 68227418HCID 68227418, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(4-chloro-2-nitro-5-(piperazin-1-yl)phenyl)-4-(dimethylamino)benzamide, 2 TFA (Preparation D, 35 mg, 0.055 mmol) in DMF (2 ml) was added 3-(2-methoxyphenyl)-5-methyl-1H-pyrazole-4-carboxylic acid (Preparation O, 15.44 mg, 0.066 mmol), HATU (25.3 mg, 0.066 mmol), followed by DIEA (0.048 ml, 0.277 mmol). The reaction was stirred at r.t. for 10 mins. Purified by prep-HPLC to afford 14 mg (33%) of the title compound. HPLC/MS (Method SZ6): (ES+) m/z (M+H)+=618; Rt=2.98 min.

Workup

  1. customPurified by prep-HPLC

Sources & evidence

ORD record
ord-07cc3626a62a4f94b1daa41a41ef509b
Source dataset
uspto-grants-2013_01
Patent number
US08362004B2

Reaction notes

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