Dimethylamine, hydrochloride → HCID 59627502, compound

HRID 1623571Notes

Reaction equation

HRID 1623571 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:14]=[C:13]([CH2:15][CH2:16][C:17]([OH:19])=O)[N:12]([C:20]3[CH:29]=[CH:28][C:23]4[O:24][CH2:25][CH2:26][O:27][C:22]=4[CH:21]=3)[N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].ON1C2C=CC=CC=2N=N1.Cl.[CH3:41][N:42](C)[CH2:43]CCN=C=NCC.C(N(C(C)C)C(C)C)C.Cl.CNC>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:14]=[C:13]([CH2:15][CH2:16][C:17]([N:42]([CH3:43])[CH3:41])=[O:19])[N:12]([C:20]3[CH:29]=[CH:28][C:23]4[O:24][CH2:25][CH2:26][O:27][C:22]=4[CH:21]=3)[N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

8

Reactant 5

HCID 10473Dimethylamine, hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59627499HCID 59627499, compound

Product 1

HCID 59627502HCID 59627502, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Compound E1 (prepared according to Ex.1) (0.00062 mol) was dissolved in DMF (5 ml). 1-Hydroxy-1H-benzotriazole (0.00186 mol), (3-Dimethylamino-propyl)-ethyl-carbodiimide.hydrochloride (1:1) (0.00186 mol) and N-ethyl-N-(1-methylethyl)-2-propanamine (0.00248 mol) were added, followed by addition of dimethylamine hydrochloride (1:1) (0.00124 mol). The reaction mixture was stirred for 3 hours at r.t. The reaction mixture was poured into water. The mixture was extracted with CHCl3. The organic layer was separated, washed with a 1M HCl solution, then washed with brine and filtered through a hydrophobic frit. The solvents were evaporated under reduced pressure to give a yellow solid residue that was dried further for one hour (in the GeneVac®). The residue was triturated with diethyl ether, filtered off and dried. Yield: 0.245 g of compound E3 (92%).

Workup

  1. extractionThe mixture was extracted with CHCl3
  2. customThe organic layer was separated
  3. washwashed with a 1M HCl solution
  4. washwashed with brine
  5. filtrationfiltered through a hydrophobic frit
  6. customThe solvents were evaporated under reduced pressure
  7. customto give a yellow solid residue that
  8. customwas dried further for one hour (in the GeneVac®)
  9. customThe residue was triturated with diethyl ether
  10. filtrationfiltered off
  11. customdried

Sources & evidence

ORD record
ord-d9c4c883756e4a72854fe4100ff9bd2f
Source dataset
uspto-grants-2014_07
Patent number
US08778974B2

Reaction notes

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