N,N-Dimethylglycine → HCID 67003419, compound

HRID 2362668Notes

Reaction equation

HRID 2362668 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.O.ON1C2C=CC=CC=2N=N1.[CH3:22][N:23]1[CH2:28]C[O:26][CH2:25][CH2:24]1.CN(C)CC(O)=O.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:25](=[O:26])[CH2:24][N:23]([CH3:28])[CH3:22])[CH2:6][CH2:5]2

Participants

8

Reactant 5

HCID 673N,N-DimethylglycineHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 34115665-Bromoindoline

Product 1

HCID 67003419HCID 67003419, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-bromoindoline (0.5 g, 2.52 mmol), 1-hydroxybenzotriazole hydrate (0.387 g, 2.52 mmol), N-methylmorpholine (1.11 mL, 10.1 mmol) and 2-(dimethylamino)acetic acid (0.299 g, 2.9 mmol) in N,N-dimethylformamide (9.5 mL) was treated with N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.678 g, 3.53 mmol) and the reaction was stirred at ambient temperature for 18 hours. The reaction was diluted with water (100 mL) and extracted with 1:1 ether/ethyl acetate (2×120 mL). The combined organic layers were washed with water (2×80 mL) and brine (2×80 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified by flash chromatography on a silica gel column eluting with a gradient of from 0% to 5% methanol in dichloromethane to provide the title compound. MS DCI (+) m/z 283.0 [M+H]+.

Workup

  1. extractionextracted with 1:1 ether/ethyl acetate (2×120 mL)
  2. washThe combined organic layers were washed with water (2×80 mL) and brine (2×80 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe concentrate was purified by flash chromatography on a silica gel column
  7. washeluting with a gradient of from 0% to 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-e312c69e500e470fb52450b0d210b7c1
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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