Dimethylamine, hydrochloride → HCID 68634168, compound

HRID 1809459Notes

Reaction equation

HRID 1809459 reaction equation
[CH3:1][O:2][C:3]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:4]=1[CH2:5][N:6]1[C:16](=[O:17])[C:15]2[N:18]3[C:8](=[C:9]([C:19]4[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=4)[N:10]=[C:11]3[CH:12]=[CH:13][CH:14]=2)[CH2:7]1.[NH:33](C)[CH3:34].Cl.[BH3-]C#N.[Na+]>ClCCCl>[CH3:1][O:2][C:3]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:4]=1[CH2:5][N:6]1[C:16](=[O:17])[C:15]2[N:18]3[C:8](=[C:9]([C:19]4[CH:20]=[CH:21][C:22]([CH2:23][NH:33][CH3:34])=[CH:25][CH:26]=4)[N:10]=[C:11]3[CH:12]=[CH:13][CH:14]=2)[CH2:7]1

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 86651540HCID 86651540, compound

Product 1

HCID 68634168HCID 68634168, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (B3) in DCE (0.1 M) was added Me2NH.HCl (8 eq.) and Ti(iPrO)4 (2.0 eq.) and the mixture stirred at RT for 12 h. To this solution, NaBH3CN (1.1 eq.) was added and stirring was continued for 12 h. The reaction mixture was quenched by the addition of sat. aq. NaHCO3, then, the aqueous phase was separated and extracted several times with DCM. The combined organic extracts were washed with brine and dried (Na2SO4). Evaporation of the solvent gave a residue of 4-(2,4-dimethoxybenzyl)-2-{4-[(methylamino)methyl]phenyl}-3,4-dihydro-5H-1,4,8b-triazaacenaphthylen-5-one which was used in the next step without further purification. MS (ES+) C26H26N4O3 requires: 442, found: 443 (M+H)+.

Workup

  1. stirringstirring
  2. waitwas continued for 12 h
  3. customThe reaction mixture was quenched by the addition of sat. aq. NaHCO3
  4. customthe aqueous phase was separated
  5. extractionextracted several times with DCM
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (Na2SO4)
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-8c77a17f39504303bda0b5d35742d23e
Source dataset
uspto-grants-2013_01
Patent number
US08362030B2

Reaction notes

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