Dimethylamine, hydrochloride → HCID 21048997, compound

HRID 2212394Notes

Reaction equation

HRID 2212394 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:26]3[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=3[F:33])[CH2:16][CH2:15][CH:14]([NH:17][S:18]([N:21]3[CH2:24][C:23](=O)[CH2:22]3)(=[O:20])=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.[CH3:35][NH:36][CH3:37].C([BH3-])#N.[Na+].C([O-])(=O)C.[Na+]>CO.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:26]3[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=3[F:33])[CH2:16][CH2:15][CH:14]([NH:17][S:18]([N:21]3[CH2:24][CH:23]([N:36]([CH3:37])[CH3:35])[CH2:22]3)(=[O:20])=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 21049002HCID 21049002, compound

Product 1

HCID 21048997HCID 21048997, compoundYield 27.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of the product from Example 185 (74 mg, 0.14 mmol.) in methanol (5 ml) was added dimethylamine hydrochloride (58 mg, 0.7 mmol.). The mixture was stirred 5 minutes, sodium cyanoborohydride (27 mg, 0.42 mmol.) and sodium acetate (34 mg, 0.4 mmol.) added, and the mixture stirred a further 18 hours at ambient temperature. Ethyl acetate (20 ml) was added and the mixture washed with 1N sodium hydroxide and brine, dried (MgSO4) and evaporated to leave a residue which was purified by column chromatography on silica, eluting with ethyl acetate to afford the desired product (21 mg). 1H NMR (CDCl3) δ 7.37 (2H, d, J=8.6 Hz), 7.32 (2H, d, J=8.6 Hz), 7.09–7.04 (2H, m), 6.88–6.81 (1H, m), 4.49 (1H, d, J=6.4 Hz), 3.87–3.78 (4H, m), 3.59 (1H, m), 3.08 (1H, m), 2.6–2.5 (2H, m), 2.41–2.33 (2H, m), 2.17 (6H, s), 2.05–2.00 (2H, m) and 1.53–1.41 (2H, m). MS (ES+) 548 ([MH]+).

Workup

  1. stirringthe mixture stirred a further 18 hours at ambient temperature
  2. washthe mixture washed with 1N sodium hydroxide and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto leave a residue which
  6. customwas purified by column chromatography on silica
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-ce13a2b3ece846f684439445d63ca9c2
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

Loading…