Stannous Chloride → 4-(4-Dimethylaminomethyl-[1,2,3]triazol-1-yl)-phenylamine

HRID 1366162Notes

Reaction equation

HRID 1366162 reaction equation
[N:1]1C=CC=CC=1C1N=NN(C2C=CC(NC3C4N(C=CN=4)C(C4C=CC(C(N)=O)=CC=4)=CN=3)=CC=2)C=1.[CH3:37][N:38]([CH3:54])[CH2:39][C:40]1[N:41]=[N:42][N:43]([C:45]2[CH:50]=[CH:49][C:48]([N+:51]([O-])=O)=[CH:47][CH:46]=2)[CH:44]=1.[Sn](Cl)Cl>C1COCC1.CCO>[NH3:1].[CH3:54][N:38]([CH2:39][C:40]1[N:41]=[N:42][N:43]([C:45]2[CH:46]=[CH:47][C:48]([NH2:51])=[CH:49][CH:50]=2)[CH:44]=1)[CH3:37]

Participants

6

Reactant 3

HCID 24479Stannous ChlorideHCID 177573324-{8-[4-(4-Pyridin-2-yl-[1,2,3]triazol-1-yl)-phenylamino]-imidazo[1,2-a]pyrazin-5-yl}-benzamideHCID 58228820N,N-Dimethyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-methanamine

Product 2

HCID 222AmmoniaHCID 590230944-(4-Dimethylaminomethyl-[1,2,3]triazol-1-yl)-phenylamineYield 59%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

In the same way as described for Compound 154, step 2 using dimethyl-[1-(4-nitro-phenyl)-1H-[1,2,3]triazol-4-ylmethyl]-amine (0.178 g, 0.722 mmol), tin(II) chloride dehydrate (0.578 g, 2.54 mmol) in (1:1) THF/EtOH (4 mL). The residue is purified on Isolute FlashSilicaII cartridge eluting with 95:5 DCM:NH3 (7M in MeOH), to afford the desired compound as a yellow solid (93.2 mg, 59%).

Workup

  1. customThe residue is purified on Isolute FlashSilicaII cartridge
  2. washeluting with 95:5 DCM

Sources & evidence

ORD record
ord-b7e688b6683547f1a92606c632f00be4
Source dataset
uspto-grants-2011_02
Patent number
US07893058B2

Reaction notes

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