Piperidin-4-ol → HCID 46864296, compound

HRID 1046537Notes

Reaction equation

HRID 1046537 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][CH2:7][O:8][C:9]1[C:10]2[N:11]([C:15]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH:25]4[CH2:30][CH2:29][CH:28]([C:31](O)=[O:32])[CH2:27][CH2:26]4)[N:19]=3)=[CH:16][N:17]=2)[CH:12]=[CH:13][CH:14]=1)(=[O:4])=[O:3].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[NH:70]1[CH2:75][CH2:74][CH:73]([OH:76])[CH2:72][CH2:71]1>CN(C=O)C.O>[OH:76][CH:73]1[CH2:74][CH2:75][N:70]([C:31]([CH:28]2[CH2:29][CH2:30][CH:25]([NH:24][C:20]3[N:19]=[C:18]([C:15]4[N:11]5[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:7][CH2:6][CH2:5][S:2]([CH3:1])(=[O:3])=[O:4])[C:10]5=[N:17][CH:16]=4)[CH:23]=[CH:22][N:21]=3)[CH2:26][CH2:27]2)=[O:32])[CH2:71][CH2:72]1

Participants

7

Reactant 4

HCID 79341Piperidin-4-olHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 66616329HCID 66616329, compound

Product 1

HCID 46864296HCID 46864296, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-{4-[8-(3-methanesulfonyl-propoxy)-imidazo[1,2-a]pyridine-3-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid (0.09 g) in DMF (3 mL) was treated with BOP (0.126 g), and the mixture stirred at RT for 15 min DIEA (0.1 mL) and piperidin-4-ol (29 mg) were added, and the mixture stirred at RT overnight. The reaction mixture was then diluted with water and stirred at RT for 30 min, permitting the product to precipitate. The resulting solid was filtered, washed with water, dried, and titurated with EtOAc. The product was filtered, dried at 50° C. under vacuum overnight to provide (4-hydroxy-piperidin-1-yl)-(4-{4-[8-(3-methanesulfonyl-propoxy)-imidazo[1,2-a]pyridin-3-yl]-pyrimidin-2-ylamino}-cyclohexyl)-methanone (compound 5, 71 mg).

Workup

  1. additionwere added
  2. stirringstirred at RT for 30 min
  3. customto precipitate
  4. filtrationThe resulting solid was filtered
  5. washwashed with water
  6. customdried
  7. filtrationThe product was filtered
  8. customdried at 50° C. under vacuum overnight

Sources & evidence

ORD record
ord-ba0a02280db94d54b0931fdb5c3bb844
Source dataset
uspto-grants-2013_10
Patent number
US08569306B2

Reaction notes

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