Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 21925537, compound

HRID 2118047Notes

Reaction equation

HRID 2118047 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.Cl.[CH3:26][N:27]1[CH2:32][CH2:31][CH:30]([C:33]([OH:35])=O)[CH2:29][CH2:28]1.[Cl:36][C:37]1[CH:62]=[CH:61][C:40]2[N:41]3[C:45]([CH2:46][NH:47][CH2:48][C:39]=2[CH:38]=1)=[N:44][N:43]=[C:42]3[CH:49]1[CH2:54][CH2:53][N:52]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][N:56]=2)[CH2:51][CH2:50]1>ClCCl>[NH3:8].[Cl:36][C:37]1[CH:62]=[CH:61][C:40]2[N:41]3[C:45]([CH2:46][N:47]([C:33]([CH:30]4[CH2:29][CH2:28][N:27]([CH3:26])[CH2:32][CH2:31]4)=[O:35])[CH2:48][C:39]=2[CH:38]=1)=[N:44][N:43]=[C:42]3[CH:49]1[CH2:50][CH2:51][N:52]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][N:56]=2)[CH2:53][CH2:54]1

Participants

6

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27600434-Piperidinecarboxylic acid, 1-methyl-, hydrochloride (1:1)HCID 113264888-Chloro-1-(3,4,5,6-tetrahydro-2h-[1,2']bipyridinyl-4-yl)-5,6-dihydro4h-2,3,5,10b-tetraaza-benzo[e]azulene

Product 2

HCID 222AmmoniaHCID 21925537HCID 21925537, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

O-(1H-Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (395 mg, 1.04 mmol) was added to a solution of 1-methylpiperidine-4-carboxylic acid hydrochloride (210 mg, 1.04 mmol) in dichloromethane (10 ml) and the solution stirred for 30 minutes. The amine from example 4 (200 mg, 0.52 mmol) was added and the reaction mixture was stirred at room temperature for 18 hours. The mixture was washed with aqueous sodium carbonate solution and the organic solution was dried over magnesium sulphate. The solution was evaporated under reduced pressure and the crude product was purified by column chromatography on silica gel using ethyl acetate:methanol:0.88 ammonia (90:10:1) as eluant, to afford the title compound as a white solid (195 mg).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 18 hours
  2. washThe mixture was washed with aqueous sodium carbonate solution
  3. dry with materialthe organic solution was dried over magnesium sulphate
  4. customThe solution was evaporated under reduced pressure
  5. customthe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6b848562bf7c45bdb9c88b1163494d3f
Source dataset
uspto-grants-2008_10
Patent number
US07442795B2

Reaction notes

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