Dimethylamine → HCID 59441760, compound

HRID 1014396Notes

Reaction equation

HRID 1014396 reaction equation
Cl.[CH3:2][C@@H:3]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([N+:14]([O-:16])=[O:15])=[C:8]([O:12][CH3:13])[CH:9]=2)[NH:4]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:24][C:25](Cl)=[O:26].[NH:28]([CH3:30])[CH3:29]>C1COCC1>[CH3:29][N:28]([CH3:30])[CH2:24][C:25]([N:4]1[C:5]2[C:10](=[CH:9][C:8]([O:12][CH3:13])=[C:7]([N+:14]([O-:16])=[O:15])[CH:6]=2)[CH2:11][C@H:3]1[CH3:2])=[O:26]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 89602Bromoacetyl chlorideHCID 67316756HCID 67316756, compound

Product 1

HCID 59441760HCID 59441760, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 0° C. slurry of (2R)-2-methyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole hydrogen chloride (4.55 g, 18.60 mmol) and K2CO3 (10.28 g, 74.4 mmol) in THF (200 mL) was treated with bromoacetyl chloride (3.10 mL, 37.2 mmol). After 2 h the reaction mixture was allowed to warm to rt. A 2M Me2NH solution in THF (55.8 mL, 112 mmol) was added and the reaction mixture was stirred at rt for 18 h. The resulting thick slurry was filtered and the solids were rinsed with EtOAc. The filtrate was concentrated onto Celite and purified by silica gel chromatography using 1-10% MeOH (containing 0.2% NH3)/CH2Cl2 to obtain N,N-dimethyl-2-[(2R)-2-methyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-2-oxoethanamine as an orange solid (2.92 g, 54%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.23 (d, J=6.04 Hz, 3H), 2.28 (s, 6H), 2.75 (d, J=17.03 Hz, 1H), 3.14 (d, J=14.83 Hz, 1H), 3.44 (d, J=14.65 Hz, 2H), 3.90 (s, 3H), 4.77-4.92 (m, 1H), 7.36 (s, 1H), 8.43 (s, 1H); ESIMS (M+H)+=294.01.

Workup

  1. filtrationThe resulting thick slurry was filtered
  2. washthe solids were rinsed with EtOAc
  3. concentrationThe filtrate was concentrated onto Celite
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-7fa39d6a2ee74643ad0f0ffd50eef931
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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