6-[4-(4-{3-[4-(Methylsulfonyl)piperazin-1-yl]propoxy}phenyl)piperidin-1-yl]-3-(trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazine → 4-{4-[2-(4-Acetylpiperazin-1-yl)ethoxy]phenyl}-1-[3-(trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-ol

HRID 2381137Notes

Reaction equation

HRID 2381137 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3([OH:38])[CH2:24][CH2:23][N:22]([C:25]4[CH:26]=[CH:27][C:28]5[N:29]([C:31]([C:34]([F:37])([F:36])[F:35])=[N:32][N:33]=5)[N:30]=4)[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].OC1C=CC(C2(O)CCN(C3C=CC4N(C(C(F)(F)F)=NN=4)N=3)CC2)=CC=1.CS(N1CCN(CCCOC2C=CC(C3CCN(C4CCC5N(C(C(F)(F)F)=NN=5)N=4)CC3)=CC=2)CC1)(=O)=O>>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]3([OH:38])[CH2:24][CH2:23][N:22]([C:25]4[CH2:26][CH2:27][C:28]5[N:29]([C:31]([C:34]([F:36])([F:37])[F:35])=[N:32][N:33]=5)[N:30]=4)[CH2:21][CH2:20]3)=[CH:17][CH:18]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 468920446-[4-(4-{3-[4-(Methylsulfonyl)piperazin-1-yl]propoxy}phenyl)piperidin-1-yl]-3-(trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazineHCID 591498284-[4-[2-(4-Acetylpiperazin-1-yl)ethoxy]phenyl]-1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-olHCID 667887034-(4-Hydroxyphenyl)-1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-ol

Product 1

HCID 468924354-{4-[2-(4-Acetylpiperazin-1-yl)ethoxy]phenyl}-1-[3-(trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-ol

Procedure

The 4-[4-[2-(4-acetylpiperazin-1-yl)ethoxy]phenyl]-1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-ol used as starting material was obtained in 55% yield by an analogous method to Example 36, preparation of starting materials, starting from 4-(4-hydroxyphenyl)-1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-ol and 2-(4-acetylpiperazine-1-yl)ethanol (obtained as described in PCT Int. Appl. WO2003064413, Example 28, preparation of starting materials).

Workup

  1. customwas obtained in 55% yield by an analogous method to Example 36, preparation of starting materials

Sources & evidence

ORD record
ord-5b65482f0a064866bc8b5c0922dd6d6b
Source dataset
uspto-grants-2012_09
Patent number
US08258140B2

Reaction notes

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