Dimethylamine, hydrochloride → HCID 89656406, compound

HRID 930915Notes

Reaction equation

HRID 930915 reaction equation
[F:1][C:2]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:6]=1[C:15]1[C:16]2[CH:25]=[C:24]([CH:26]=O)[NH:23][C:17]=2[C:18](=[O:22])[N:19]([CH3:21])[CH:20]=1.Cl.[CH3:34][NH:35][CH3:36].C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[F:1][C:2]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:12])=[O:13])=[CH:7][C:6]=1[C:15]1[C:16]2[CH:25]=[C:24]([CH2:26][N:35]([CH3:36])[CH3:34])[NH:23][C:17]=2[C:18](=[O:22])[N:19]([CH3:21])[CH:20]=1

Participants

6

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 89657403HCID 89657403, compound

Product 1

HCID 89656406HCID 89656406, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution of Example 278a (0.20 g, 0.44 mmol) and dimethylamine hydrochloride (0.071 g, 0.873 mmol) in methanol (6 mL) was added zinc chloride (0.059 g, 0.436 mmol) at ambient temperature. The reaction mixture was stirred at ambient temperature for one hour, and then sodium cyanoborohydride (0.055 g, 0.873 mmol) was added and the reaction mixture was stirred at ambient temperature for three days. The resulting solid was filtered and washed with methanol (10 mL), and the eluant was concentrated. The residue was purified by preparative thin layer chromatography (silica gel, dichloromethane/methanol, 15/1) to provide the title compound (75 mg, 34% yield). 1H NMR (400 MHz, CD3OD) δ ppm 8.07 (d, J=2.4 Hz, 1H), 7.94 (dd, J=2.4, 6.4 Hz, 1H), 7.38 (s, 1H), 7.25-7.06 (m, 2H), 7.04-6.98 (m, 2H), 6.31 (s, 1H), 3.71 (s, 3H), 3.67 (s, 2H), 3.19 (s, 3H), 2.28 (s, 6H). MS (ESI+) m/z 488.1 (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for three days
  2. filtrationThe resulting solid was filtered
  3. washwashed with methanol (10 mL)
  4. concentrationthe eluant was concentrated
  5. customThe residue was purified by preparative thin layer chromatography (silica gel, dichloromethane/methanol, 15/1)

Sources & evidence

ORD record
ord-f7ddaea5598f497a8100addab17c2e28
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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