1-Methyl-1H-indole-3-carbaldehyde → 6-[4-[(1-Methylindol-3-yl)methyl]piperazin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine

HRID 1674835Notes

Reaction equation

HRID 1674835 reaction equation
[N:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([C:16]([F:19])([F:18])[F:17])=[N:14][N:15]=3)[N:12]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:20][N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([CH:30]=O)=[CH:22]1>>[CH3:20][N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([CH2:30][N:4]2[CH2:3][CH2:2][N:1]([C:7]3[CH:8]=[CH:9][C:10]4[N:11]([C:13]([C:16]([F:17])([F:18])[F:19])=[N:14][N:15]=4)[N:12]=3)[CH2:6][CH2:5]2)=[CH:22]1

Participants

3

Reactant 2

HCID 878941-Methyl-1H-indole-3-carbaldehydeHCID 14768626-Piperazino-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine

Product 1

HCID 673406086-[4-[(1-Methylindol-3-yl)methyl]piperazin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine

Procedure

Reductive amination of 6-(piperazin-1-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine with 1-methylindole-3-carbaldehyde was carried out according to General Synthetic Method 5. The crude product was purified by hplc using a Waters XBridge Prep C18 OBD column (5μ silica, 19 mm diameter, 100 mm length) eluted with decreasingly polar mixtures of water (containing 1% aqueous ammonia) and acetonitrile as eluents to give 6-[4-[(1-methylindol-3-yl)methyl]piperazin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine.

Workup

  1. customThe crude product was purified by hplc
  2. washeluted with decreasingly polar mixtures of water (containing 1% aqueous ammonia) and acetonitrile as eluents

Sources & evidence

ORD record
ord-83d60791f26446f2abe8e0d06c60ae1d
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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