Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 66692939, compound

HRID 1808892Notes

Reaction equation

HRID 1808892 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:10]=[N:11][N:12]([CH3:17])[C:13]=1[C:14]([OH:16])=O.[Cl:18][C:19]1[C:24]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:23][C:22]([NH:31][C:32](=[O:43])[C:33]2[CH:38]=[CH:37][C:36]([CH2:39][N:40]([CH3:42])[CH3:41])=[CH:35][CH:34]=2)=[C:21]([N+:44]([O-:46])=[O:45])[CH:20]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C1C=CN=CC=1)C.CN1C(=O)CCC1>[Cl:18][C:19]1[C:24]([N:25]2[CH2:26][CH2:27][N:28]([C:14]([C:13]3[N:12]([CH3:17])[N:11]=[N:10][C:9]=3[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])=[O:16])[CH2:29][CH2:30]2)=[CH:23][C:22]([NH:31][C:32](=[O:43])[C:33]2[CH:34]=[CH:35][C:36]([CH2:39][N:40]([CH3:42])[CH3:41])=[CH:37][CH:38]=2)=[C:21]([N+:44]([O-:46])=[O:45])[CH:20]=1

Participants

6

Reactant 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66691672HCID 66691672, compoundHCID 66693726HCID 66693726, compound

Product 1

HCID 66692939HCID 66692939, compoundYield 25.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 4-(2-methoxyphenyl)-1-methyl-1H-1,2,3-triazole-5-carboxylic acid (44.7 mg, 0.192 mmol), N-(4-chloro-2-nitro-5-(piperazin-1-yl)phenyl)-4-((dimethylamino)methyl)benzamide (85 mg, 0.160 mmol), HATU (79 mg, 0.208 mmol), and DMAP (78 mg, 0.639 mmol) in NMP (2 mL) was stirred for 3 h. HPLC purification, then silica column purification afforded the title compound (28 mg, 0.041 mmol). 1H-NMR (CDCl3, 500 MHz): δ11.62 (1H, s), 8.57 (1H, s), 8.31 (1H, s), 8.06 (2H, d, J=8.24 Hz), 7.81 (1H, d, J=7.24 Hz), 7.69 (2H, d, J=7.93 Hz), 7.43 (1H, t, J=8.24 Hz), 7.13 (1H, t, J=7.32 Hz), 7.01 (1H, d, J=7.24 Hz), 4.28 (2H, s), 4.20 (2H, s), 3.94 (2H, m), 3.83 (3H, s), 3.25 (4H, s), 2.83 (6H, s), 2.68 (2H, m). HPLC/MS (Method J): (ES+) m/z (M+H)+=633; Rt=1.52 min.

Workup

  1. customHPLC purification
  2. customsilica column purification

Sources & evidence

ORD record
ord-4b5d99899ec94676bc4ac22b6fbfe6d3
Source dataset
uspto-grants-2013_01
Patent number
US08362004B2

Reaction notes

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