Tetrafluoro-m-phenylenediamine dihydrochloride → 2-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-8-((trans)-3-fluoropiperidin-4-yloxy)quinoline dihydrochloride

HRID 2035651Notes

Reaction equation

HRID 2035651 reaction equation
C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:13].Cl.F[C@H]1[C@H](OC2C=CC=C3C=2N=CC=C3)CCNC1.[N:33]1[N:34]=[C:35]([C:42]2[CH:51]=[CH:50][C:49]3[C:44](=[C:45]([O:52][C@@H:53]4[CH2:58][CH2:57][NH:56][CH2:55][C@H:54]4[F:59])[CH:46]=[CH:47][CH:48]=3)[N:43]=2)[N:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=12>O>[ClH:13].[ClH:13].[N:33]1[N:34]=[C:35]([C:42]2[CH:51]=[CH:50][C:49]3[C:44](=[C:45]([O:52][C@@H:53]4[CH2:58][CH2:57][NH:56][CH2:55][C@H:54]4[F:59])[CH:46]=[CH:47][CH:48]=3)[N:43]=2)[N:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=12

Participants

5

Reactant 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 667820318-((trans)-3-Fluoropiperidin-4-yloxy)quinolineHCID 672301232-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-8-((trans)-3-fluoropiperidin-4-yloxy)quinoline

Product 1

HCID 672344752-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-8-((trans)-3-fluoropiperidin-4-yloxy)quinoline dihydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Preparation of the dihydrochloride salt of Enantiomer 2 of 2-k [1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-((trans)-3-fluoropiperidin-4-yloxy)quinoline: Prepared as described in Example 94 using non-racemic 2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-((trans)-3-fluoropiperidin-4-yloxy)quinoline in Step 4C. Specific rotation: [α]20D=+2.7° (c=0.45, 1:1 water/95% ethanol).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-992da550797e48229e0b30463ce69240
Source dataset
uspto-grants-2013_11
Patent number
US08575145B2

Reaction notes

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