Diisopropylethylamine → HCID 178511290, compound

HRID 528689Notes

Reaction equation

HRID 528689 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[N:3]=[N:2]1.ClC(N(C)C)=C(C)C.Cl.[NH2:18][CH2:19][C:20]([N:22]1[CH2:26][CH2:25][CH2:24][C@H:23]1[C:27]#[N:28])=[O:21].C(N(C(C)C)C(C)C)C>O1CCOCC1>[C:27]([C@@H:23]1[CH2:24][CH2:25][CH2:26][N:22]1[C:20](=[O:21])[CH2:19][NH:18][C:6]([C:4]1[NH:3][N:2]=[N:1][CH:5]=1)=[O:8])#[N:28]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1401204-Carboxy-1,2,3-triazoleHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 86648337HCID 86648337, compound

Product 1

HCID 178511290HCID 178511290, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1H-1,2,3-triazole-4-carboxylic acid (0.092 g, 0.814 mmol) was dispersed in dry dioxane (3 mL) in a round bottom flask with nitrogen. To this 1-chloro-N,N,2-trimethylprop-1-en-1-amine (0.151 ml, 1.139 mmol) was added and the reaction was stirred for 30 minutes at room temperature. The starting material dissolves over time. Then (S)-1-(2-aminoacetyl)pyrrolidine-2-carbonitrile hydrochloride (0.247 g, 1.302 mmol) with N-ethyl-N-isopropylpropan-2-amine (0.307 ml, 1.709 mmol) was added and the mixture was stirred for 2 h, evaporated to dryness and redissolved in ethyl acetate. Followed by washing with 0.1N citric acid and saturated sodium bicarbonate and brine. After drying over sodium sulfate, filtration and evaporation, the product was purified using column chromatography.

Workup

  1. dissolutionThe starting material dissolves over time
  2. stirringthe mixture was stirred for 2 h
  3. customevaporated to dryness
  4. dissolutionredissolved in ethyl acetate
  5. washFollowed by washing with 0.1N citric acid and saturated sodium bicarbonate and brine
  6. dry with materialAfter drying over sodium sulfate, filtration and evaporation
  7. customthe product was purified

Sources & evidence

ORD record
ord-a5215b8d4711452584b5a93bf7a93f17
Source dataset
uspto-grants-2016_05
Patent number
US09346814B2

Reaction notes

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