Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 1-[8-Chloro-1-(3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulen-5-yl]-3-dimethylamino-propan-1-one

HRID 1243591Notes

Reaction equation

HRID 1243591 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]([CH3:33])[CH2:28][CH2:29][C:30](O)=[O:31].[Cl:34][C:35]1[CH:60]=[CH:59][C:38]2[N:39]3[C:43]([CH2:44][NH:45][CH2:46][C:37]=2[CH:36]=1)=[N:42][N:41]=[C:40]3[CH:47]1[CH2:52][CH2:51][N:50]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][N:54]=2)[CH2:49][CH2:48]1>ClCCl>[NH3:8].[Cl:34][C:35]1[CH:60]=[CH:59][C:38]2[N:39]3[C:43]([CH2:44][N:45]([C:30](=[O:31])[CH2:29][CH2:28][N:27]([CH3:33])[CH3:26])[CH2:46][C:37]=2[CH:36]=1)=[N:42][N:41]=[C:40]3[CH:47]1[CH2:48][CH2:49][N:50]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][N:54]=2)[CH2:51][CH2:52]1

Participants

6

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (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]azuleneHCID 115863273-(Dimethylamino)propanoic acid hydrochloride

Product 2

HCID 222AmmoniaHCID 219256491-[8-Chloro-1-(3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulen-5-yl]-3-dimethylamino-propan-1-oneYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

O-(1H-Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (200 mg, 0.52 mmol) was added to a solution of 3-dimethylaminopropionic acid hydrochloride (80 mg, 0.52 mmol) in dichloromethane (5 ml) and the solution was stirred for 15 minutes. The amine from example 4 (100 mg, 0.26 mmol) was added and the reaction mixture was stirred at room temperature for 18 hours. The mixture was partitioned between dichloromethane and aqueous sodium bicarbonate solution, and the layers were separated. The organic phase was dried over magnesium sulphate and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (90:10:1), to afford the title compound as a white solid (110 mg).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 18 hours
  2. customThe mixture was partitioned between dichloromethane and aqueous sodium bicarbonate solution
  3. customthe layers were separated
  4. dry with materialThe organic phase was dried over magnesium sulphate
  5. customevaporated under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-1fc06ea91f2d4cbfa48226d6a786e9aa
Source dataset
uspto-grants-2006_10
Patent number
US07119088B2

Reaction notes

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