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Dimethylformamide → 4-[3-((2S,6R)-2,6-Dimethyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-cyclohexylamine

HRID 2200046
Notes
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Reaction equation

HRID 2200046 reaction equation
[H-].[Na+].[NH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([OH:10])[CH2:6][CH2:5]1.F[C:12]1[CH:13]=[CH:14][C:15]2[N:16]([C:18]([N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][C@@H:22]3[CH3:27])=[N:19][N:20]=2)[CH:17]=1.[CH3:28]N(C=O)C>>[CH3:27][C@H:22]1[CH2:23][CH2:24][CH2:25][C@@H:26]([CH3:28])[N:21]1[C:18]1[N:16]2[CH:17]=[C:12]([O:10][CH:7]3[CH2:8][CH2:9][CH:4]([NH2:3])[CH2:5][CH2:6]3)[CH:13]=[CH:14][C:15]2=[N:20][N:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 866871056-Fluoro-3-((S)-2-methyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridineHCID 178511715HCID 178511715, compound

Product 1

HCID 1177290354-[3-((2S,6R)-2,6-Dimethyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-cyclohexylamineYield 27%

Procedure

Sodium hydride (60% in mineral oil, 0.26 g, 6.39 mmol) was added to a stirred solution of trans-4-amino cyclohexanol (0.397 g, 3.45 mmol) in anhydrous DMF (10 mL) at RT under an argon atmosphere. The reaction mixture was stirred at RT for 30 min, then Intermediate 2d (0.50 g, 2.13 mmol) in anhydrous DMF (4 mL) was added and stirred at 60° C. for 10 h. After cooling, the reaction mixture was quenched by careful addition of a saturated aqueous solution of NH4Cl and water (1:1) and extracted with EtOAc and then DCM. The combined organic extracts were concentrated in vacuo and the resultant residue was purified by FCC, using 0-25% [2M NH3 in MeOH] in DCM, to afford the title compound (0.193 g, 27%) as an orange residue. LCMS (Method 3): Rt 2.00 min, m/z 330 [MH+].

Workup

  1. stirringstirred at 60° C. for 10 h
  2. temperatureAfter cooling
  3. customthe reaction mixture was quenched by careful addition of a saturated aqueous solution of NH4Cl and water (1:1)
  4. extractionextracted with EtOAc
  5. concentrationThe combined organic extracts were concentrated in vacuo
  6. customthe resultant residue was purified by FCC

Sources & evidence

ORD record
ord-2b30c960f306467ebcbbe8bf7635586b
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09359354B2

Reaction notes

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