Dimethylamine → Cycloechinulin

HRID 1185994Notes

Reaction equation

HRID 1185994 reaction equation
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2N=N1.ON1C2C=CC=C[C:29]=2N=N1.[CH3:35][O:36][C:37]([C:39]1[CH:40]=[CH:41][C:42]2[N:43]([C:45]([CH2:55][C:56]([OH:58])=O)(C3C=CC(C)=CC=3)[CH2:46][N:47]=2)[CH:44]=1)=[O:38].[CH3:59][NH:60][CH3:61]>ClCCl>[CH3:59][N:60]([CH3:61])[C:56]([CH2:55][C:45]1[N:43]2[CH:44]=[C:39]([C:37]([O:36][CH3:35])=[O:38])[CH:40]=[CH:41][C:42]2=[N:47][C:46]=1[C:11]1[CH:12]=[CH:13][C:14]([CH3:29])=[CH:15][CH:16]=1)=[O:58]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67357839HCID 67357839, compound

Product 1

HCID 16088234CycloechinulinYield 133.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

O-(1H-Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (7.752 g, 20.48 mmol), 1-hydroxybenzotriazole (0.92 g, 6.8 mmol) and n,n-ethyldiisopropylamine (4.8 ml, 27.76 mmol) were added to a suspension of 5 (4.4 g, 13.6 mmol) in dichloromethane (200 ml). The solution was stirred for 30 min under nitrogen, dimethylamine (2M in THF, 9.33 ml, 28.0 mmol) added and the mixture stirred at room temperature for 3 hr. Dichloromethane (200 ml) was added, and the solution washed with HCl (0.5M), saturated NaCl solution, and 10% NaHCO3 solution. The organic phase was dried over MgSO4 and solvent evaporated to give a light cream solid methyl 3-dimethylcarbamoylmethyl-2-(4-tolyl)imidazo[1,2-a]pyridine-6-carboxylate 6 (3.2 g, 67%).

Workup

  1. stirringthe mixture stirred at room temperature for 3 hr
  2. washthe solution washed with HCl (0.5M), saturated NaCl solution, and 10% NaHCO3 solution
  3. dry with materialThe organic phase was dried over MgSO4 and solvent
  4. customevaporated

Sources & evidence

ORD record
ord-b65dc98bc78f40989e057a66b473416e
Source dataset
uspto-grants-2014_03
Patent number
US08673652B2

Reaction notes

Loading…