Triethylamine → HCID 136341306, compound

HRID 1506170Notes

Reaction equation

HRID 1506170 reaction equation
[F:1][C:2]([F:8])([F:7])[CH2:3][C:4](O)=[O:5].Cl.CN(C)CC[CH2:14][N:15]=[C:16]=[N:17][CH2:18][CH3:19].O[N:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[N:23]1.[CH2:31]([N:33](CC)CC)[CH3:32]>O>[C:25]1([CH:30]2[CH2:29][CH2:28][N:33]([C:4](=[O:5])[CH2:3][C:2]([F:8])([F:7])[F:1])[CH2:31][CH2:32]2)[N:24]=[N:23][N:22]2[C:26]=1[C:27]1[CH:19]=[CH:18][NH:17][C:16]=1[N:15]=[CH:14]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27779723,3,3-Trifluoropropionic acid

Product 1

HCID 136341306HCID 136341306, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

1-(Piperidin-4-yl)-7H-pyrrolo[3,2-e][1,2,3]triazolo[1,5-c]pyrimidine acetate (30.0 mg, 0.0992 mmol) obtained in Reference Synthetic Examplea 104 in N,N-dimethylformamide (1 mL) was stirred with 3,3,3-trifluoropropionic acid (14.0 μL, 0.161 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (48.0 mg, 0.248 mmol), 1-hydroxybenzotriazole (34.0 mg, 0.248 mmol) and triethylamine (43.0 μL, 0.310 mmol) at room temperature for 3 hours and then with water (1 mL) for another 1 day. After addition of water, the reaction mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1 (v/v)) to give the title compound as a colorless solid (11.7 mg, yield 34%).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1 (v/v))

Sources & evidence

ORD record
ord-7600ed5778994884a7d039ca00044cf6
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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