Dimethylamine → HCID 59442138, compound

HRID 1014400Notes

Reaction equation

HRID 1014400 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 67316649HCID 67316649, compound

Product 1

HCID 59442138HCID 59442138, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A slurry of (2S)-2-methyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole hydrogen chloride (4.43 g, 18.11 mmol) and K2CO3 (10.01 g, 72.4 mmol) in THF (200 mL) at 0° C. was treated with bromoacetyl chloride (3.02 mL, 36.2 mmol). After 2 h the resulting mixture was allowed to warm to rt. A 2M Me2NH solution in THF (54.3 mL, 109 mmol) was added. After 18 h the resulting thick slurry was filtered and the solids were washed with EtOAc. The filtrate was concentrated onto Celite and purified by silica gel chromatography using 1-10% MeOH (containing 0.2% NH3)/CH2Cl2. The foamy oily product was chased using CH2Cl2 and hexanes, CH2Cl2 and Et2O, then Et2O to obtain N,N-dimethyl-2-[(2S)-2-methyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-2-oxoethanamine as an orange solid (2.50 g, 47%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.23 (d, J=6.04 Hz, 3H), 2.28 (s, 6H), 2.75 (d, J=17.21 Hz, 1H), 3.14 (d, J=14.65 Hz, 1H), 3.44 (d, J=14.65 Hz, 2H), 3.90 (s, 3H), 4.75-4.92 (m, 1H), 7.37 (s, 1H), 8.43 (s, 1H); ESIMS (M+H)+=293.88.

Workup

  1. filtrationAfter 18 h the resulting thick slurry was filtered
  2. washthe solids were washed with EtOAc
  3. concentrationThe filtrate was concentrated onto Celite
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-ed9222dae2f6412681ace78cb788a488
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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