4-{1-[3-(Trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl}phenol → 6-[4-(4-{2-[(3S)-4-acetyl-3-methylpiperazin-1-yl]ethoxy}phenyl)piperidin-1-yl]-3-(trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazine

HRID 2381144Notes

Reaction equation

HRID 2381144 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[N:7]2[N:8]=[C:9]([N:12]3[CH2:17][CH2:16][CH:15]([C:18]4[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=4)[CH2:14][CH2:13]3)[CH2:10][CH2:11][C:6]2=[N:5][N:4]=1.[C:27]([N:30]1[CH2:35][CH2:34][N:33]([CH2:36][CH2:37]O)[CH2:32][C@@H:31]1[CH3:39])(=[O:29])[CH3:28]>>[C:27]([N:30]1[CH2:35][CH2:34][N:33]([CH2:36][CH2:37][O:24][C:21]2[CH:20]=[CH:19][C:18]([CH:15]3[CH2:16][CH2:17][N:12]([C:9]4[CH2:10][CH2:11][C:6]5[N:7]([C:3]([C:2]([F:1])([F:25])[F:26])=[N:4][N:5]=5)[N:8]=4)[CH2:13][CH2:14]3)=[CH:23][CH:22]=2)[CH2:32][C@@H:31]1[CH3:39])(=[O:29])[CH3:28]

Participants

3

Reactant 2

HCID 685004304-{1-[3-(Trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl}phenolHCID 68504459(S)-2-(4-acetyl-3-methylpiperazin-1-yl)ethanol

Product 1

HCID 468925686-[4-(4-{2-[(3S)-4-acetyl-3-methylpiperazin-1-yl]ethoxy}phenyl)piperidin-1-yl]-3-(trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazineYield 41%

Procedure

Obtained in 41% yield by an analogous method to Example 51, starting from 4-{1-[3-(trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl}phenol and (S)-2-(4-acetyl-3-methylpiperazin-1-yl)ethanol (obtained by an analogous method to the R enantiomer as described in Example 51, preparation of starting materials).

Workup

  1. customObtained in 41% yield by an analogous method to Example 51
  2. customobtained by an analogous method to the R enantiomer
  3. customas described in Example 51, preparation of starting materials)

Sources & evidence

ORD record
ord-333b07a67f264d2cb4fad15660f5b9c6
Source dataset
uspto-grants-2012_09
Patent number
US08258140B2

Reaction notes

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