4-Piperidinol, 1-methyl- → HCID 22594109, compound

HRID 1760980Notes

Reaction equation

HRID 1760980 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][C:16]([C:18]3[C:23]4[O:24][C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=5[C:22]=4[CH:21]=[CH:20][CH:19]=3)=[O:17])[CH:12]=[CH:11][C:10]=2[CH3:31])[CH:5]=[CH:4][N:3]=1.[OH:32][CH:33]1[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]1>>[CH:21]1[C:22]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[O:24][C:23]=2[C:18]([C:16]([NH:15][C:13]2[CH:12]=[CH:11][C:10]([CH3:31])=[C:9]([CH:14]=2)[NH:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([O:32][CH:33]3[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]3)[N:7]=2)=[O:17])=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 660484-Piperidinol, 1-methyl-HCID 225940952-Chloro-4-[5-(4-dibenzofuranylcarbonylamino)-2-methylanilino]pyrimidine

Product 1

HCID 22594109HCID 22594109, compound

Procedure

Using an analogous procedure to that described in Example 8, 2-chloro-4-[5-(4-dibenzofuranylcarbonylamino)-2-methylanilino]pyrimidine was reacted with 4-hydroxy-N-methylpiperidine. The reaction mixture was evaporated and the residue was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and methanol as eluent followed by increasingly polar mixtures of methylene chloride and methanol containing 1% aqueous ammonium hydroxide solution. There was thus obtained the title compound; NMR Spectrum: (DMSOd6) 1.56 (m, 2H), 1.84-2.1 (m, 4H), 1.97 (s, 3H), 2.17 (s, 3H), 2.53 (m, 2H), 4.78 (m, 1H), 6.22 (d, 1H), 7.18 (d, 1H), 7.38-7.58 (m, 4H), 7.77 (d, 1H), 7.86 (m, 2H), 7.93 (d, 1H), 8.19 (d, 1H), 8.28 (d, 1H); Mass Spectrum: M+H+ 507.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was purified by column chromatography on silica using
  3. temperatureincreasingly polar mixtures of methylene chloride and methanol as eluent
  4. temperatureby increasingly polar mixtures of methylene chloride and methanol containing 1% aqueous ammonium hydroxide solution

Sources & evidence

ORD record
ord-cfafc1dc351c4c1997052a9e3aa6625b
Source dataset
uspto-grants-2005_01
Patent number
US06846827B1

Reaction notes

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