Piperidin-4-ol → HCID 46896573, compound

HRID 1046538Notes

Reaction equation

HRID 1046538 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[N:18]=[C:17]([C:19]3[N:23]4[CH:24]=[CH:25][CH:26]=[C:27]([O:28][CH2:29][C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[C:22]4=[N:21][CH:20]=3)[CH:16]=[CH:15][N:14]=2)[CH2:8][CH2:7]1)=O)C.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:72]1[CH2:77][CH2:76][CH:75]([OH:78])[CH2:74][CH2:73]1>CN(C=O)C.O>[CH2:29]([O:28][C:27]1[C:22]2[N:23]([C:19]([C:17]3[CH:16]=[CH:15][N:14]=[C:13]([NH:12][CH:9]4[CH2:10][CH2:11][CH:6]([C:4]([N:72]5[CH2:77][CH2:76][CH:75]([OH:78])[CH2:74][CH2:73]5)=[O:3])[CH2:7][CH2:8]4)[N:18]=3)=[CH:20][N:21]=2)[CH:24]=[CH:25][CH:26]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

7

Reactant 4

HCID 79341Piperidin-4-olHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 46896668HCID 46896668, compound

Product 1

HCID 46896573HCID 46896573, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-[4-(8-benzyloxy-imidazo[1,2-a]pyridine-3-yl)-pyrimidin-2-ylamino]-cyclohexanecarboxylic acid ethyl ester (0.23 g) in DMF (10 mL) was treated with BOP (79 mg), then DIEA (0.345 g), then piperidin-4-ol (79 mg), and the mixture stirred at RT for 5 h. The reaction mixture was then diluted with water, and the resulting solid filtered, washed with water, and dried. The solid was then dissolved in hot EtOAc, MeOH, and DCM, and the solution filtered hot. The product was dried at 50° C. under vacuum overnight to provide {4-[4-(8-benzyloxy-imidazo[1,2-a]pyridin-3-yl)-pyrimidin-2-ylamino]-cyclohexyl}-(4-hydroxy-piperidin-1-yl)-methanone (compound 6, 244 mg).

Workup

  1. filtrationthe resulting solid filtered
  2. washwashed with water
  3. customdried
  4. dissolutionThe solid was then dissolved in hot EtOAc
  5. filtrationMeOH, and DCM, and the solution filtered hot
  6. customThe product was dried at 50° C. under vacuum overnight

Sources & evidence

ORD record
ord-184cc23c4a6e481aaa50f1d50ba341c2
Source dataset
uspto-grants-2013_10
Patent number
US08569306B2

Reaction notes

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