Dimethylformamide → HCID 67355700, compound

HRID 522885Notes

Reaction equation

HRID 522885 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([NH:14][CH3:15])=[O:13])[N:3]=1.CN(C=O)C.C(N(C(C)C)C(C)C)C.[NH:33]1[CH2:38][CH2:37][CH:36]([OH:39])[CH2:35][CH2:34]1>CO.C(Cl)Cl>[NH4+:3].[OH-:13].[OH:39][CH:36]1[CH2:37][CH2:38][N:33]([C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]3[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=3)[C:12]([NH:14][CH3:15])=[O:13])[N:3]=2)[CH2:34][CH2:35]1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 79341Piperidin-4-olHCID 81531DiisopropylethylamineHCID 77230956HCID 77230956, compound

Product 2

HCID 14923Ammonium HydroxideHCID 67355700HCID 67355700, compoundYield 160.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

3-(4-Chloro-1,3,5-triazin-2-ylamino)-N-methylbenzamide (200 mg, 0.758 mmol) was dissolved in DMF (3034 μL, 0.758 mmol) at RT. To this solution was added N-ethyl-N-isopropylpropan-2-amine (145 μL, 0.834 mmol) and piperidin-4-ol (77 mg, 0.758 mmol). The resulting mixture was stirred at RT for 1 h, at which time LCMS showed mainly product. The reaction mixture was passed through an SCX-2 column with MeOH. The product was then eluted with 2.0 M NH3 in MeOH. After concentration, the crude was purified further by medium pressure silica gel chromatography using 60:40 CH2Cl2:(90:10:1 CH2Cl2:MeOH:NH4OH) as the eluent to afford 3-(4-(4-hydroxypiperidin-1-yl)-1,3,5-triazin-2-ylamino)-N-methylbenzamide (200 mg, 0.609 mmol, 80%) as a white solid.

Workup

  1. washThe product was then eluted with 2.0 M NH3 in MeOH
  2. concentrationAfter concentration
  3. customthe crude was purified further by medium pressure silica gel chromatography

Sources & evidence

ORD record
ord-d2f9763967024b9ab5caace124abeefa
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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