Pyridine → HCID 86686781, compound

HRID 1403146Notes

Reaction equation

HRID 1403146 reaction equation
[F:1][CH:2]([F:32])[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([NH:20][CH2:21][CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[N:9]=2)[C:6]2[CH:28]=[CH:29][CH:30]=[CH:31][C:5]=2[N:4]=1.N1C=CC=CC=1.[C:39](OC(=O)C)(=[O:41])[CH3:40]>C1(C)C=CC=CC=1>[C:39]([N:25]1[CH2:24][CH2:23][CH:22]([CH2:21][NH:20][C:10]2[N:9]=[C:8]([N:7]3[C:6]4[CH:28]=[CH:29][CH:30]=[CH:31][C:5]=4[N:4]=[C:3]3[CH:2]([F:1])[F:32])[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=2)[CH2:27][CH2:26]1)(=[O:41])[CH3:40]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 86686782HCID 86686782, compound

Product 1

HCID 86686781HCID 86686781, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-morpholin-4-yl-N-(piperidin-4-ylmethyl)-1,3,5-triazin-2-amine (50 mg) and pyridine (2 mL) was added acetic anhydride (14 μL), and the mixture was stirred at room temperature overnight. To the reaction mixture was added toluene, followed by concentrating under reduced pressure. The residue was dissolved in dichloromethane, and silica gel was added thereto, followed by concentrating under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate, and subsequently chloroform:methanol) to obtain N-[(1-acetylpiperidin-4-yl)methyl]-4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazine-2-amine (44 mg) as a white powder.

Workup

  1. concentrationby concentrating under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane
  3. additionsilica gel was added
  4. concentrationby concentrating under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-c439e1e4e98f4b2ba292b722bc99b63d
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

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