N,N-Dimethylglycine → HCID 67003626, compound

HRID 2362745Notes

Reaction equation

HRID 2362745 reaction equation
[Cl:1][C:2]1[C:3]([C:27]2[S:31][C:30]([C:32]3([OH:36])[CH2:35][O:34][CH2:33]3)=[N:29][CH:28]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=3)[N:8]([S:17]([C:20]3[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:5]2=[N:6][CH:7]=1.[CH3:37][N:38]([CH3:43])[CH2:39][C:40](O)=[O:41].CN1CCOCC1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[Cl:1][C:2]1[C:3]([C:27]2[S:31][C:30]([C:32]3([OH:36])[CH2:35][O:34][CH2:33]3)=[N:29][CH:28]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH2:12][CH2:13][N:14]([C:40](=[O:41])[CH2:39][N:38]([CH3:43])[CH3:37])[CH2:15][CH:16]=3)[N:8]([S:17]([C:20]3[CH:21]=[CH:22][C:23]([CH3:24])=[CH:25][CH:26]=3)(=[O:18])=[O:19])[C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 673N,N-DimethylglycineHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67002767HCID 67002767, compound

Product 1

HCID 67003626HCID 67003626, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 146C (0.048 g, 0.088 mmol), 2-(dimethylamino)acetic acid (0.011 g, 0.102 mmol), N-methylmorpholine (0.019 mL, 0.177 mmol), and 1-hydroxybenzotriazole hydrate (0.007 g, 0.044 mmol) in N,N-dimethylformamide (1 mL) was treated with N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.025 g, 0.133 mmol), and the reaction was stirred at ambient temperature for 6 hours. The reaction was partitioned between ethyl acetate and water. The aqueous layer was extracted with additional ethyl acetate. The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The material was used directly in the next step without further purification. MS APCI(+) m/z 627.4 [M+H]+.

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. extractionThe aqueous layer was extracted with additional ethyl acetate
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe material was used directly in the next step without further purification

Sources & evidence

ORD record
ord-38bc4f1df3654baba11adfd3f78fcbc8
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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