Sodium Carbonate → N,N-Dimethyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-methanamine

HRID 1921786Notes

Reaction equation

HRID 1921786 reaction equation
[N:1]1C=CC=CC=1C1[N:8]=[N:9][N:10](C2C=CC(NC3C4N(C=CN=4)C(C4C=CC(C(N)=O)=CC=4)=CN=3)=CC=2)C=1.I[C:38]1[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][CH:39]=1.[CH3:47][N:48]([CH3:52])[CH2:49][C:50]#[CH:51].N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[Na+].[Na+].[N-]=[N+]=[N-].[Na+].[Na].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O>O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].CS(C)=O.O>[NH3:1].[CH3:47][N:48]([CH3:52])[CH2:49][C:50]1[N:8]=[N:9][N:10]([C:38]2[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][CH:39]=2)[CH:51]=1

Participants

11

Reactant 7

HCID 10340Sodium CarbonateHCID 124951-Iodo-4-nitrobenzeneHCID 33557Sodium AzideHCID 81643N,N-DimethylpropargylamineHCID 145742L-ProlineHCID 177573324-{8-[4-(4-Pyridin-2-yl-[1,2,3]triazol-1-yl)-phenylamino]-imidazo[1,2-a]pyrazin-5-yl}-benzamideHCID 178519209sodium (L)-ascorbate

Product 2

HCID 222AmmoniaHCID 58228820N,N-Dimethyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-methanamineYield 36%

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalystHCID 23503278(Methanesulfinyl)methane--water (1/1)Solvent

Procedure

In the same way as described for Compound 154, step 1 using 1-iodo-4-nitrobenzene (0.498 g, 2.0 mmol), 1-dimethylamino-2-propyne (0.216 mL, 2.00 mmol), L-proline (46.1 mg, 0.40 mmol), Na2CO3 (42.4 mg, 0.40), NaN3 (0.156 g, 2.40 mmol), (+)-sodium-L-ascorbate (39.7 mg, 0.20 mmol), copper(II) sulphate pentahydrate (16.0 mg, 0.10 mmol) in 9:1 DMSO-water (4 mL). The residue is purified on Isolute FlashSilicaII cartridge eluting with 97:3 DCM:NH3 (7M in MeOH), to afford the title compound as a brown solid (0.179 g, 36%).

Workup

  1. customThe residue is purified on Isolute FlashSilicaII cartridge
  2. washeluting with 97:3 DCM

Sources & evidence

ORD record
ord-fbf3691028304ecdadfa1da7973405db
Source dataset
uspto-grants-2012_05
Patent number
US08173656B2

Reaction notes

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