Triethylamine → HCID 53373668, compound

HRID 1500781Notes

Reaction equation

HRID 1500781 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([NH:7][C:8]2[CH:13]=[N:12][CH:11]=[C:10]([C:14]3[CH:15]=[N:16][N:17]4[CH:22]=[CH:21][N:20]=[CH:19][C:18]=34)[N:9]=2)[CH2:2]1.O=C1CCC(=O)N1[O:30][C:31](=O)[CH2:32][C:33]#[N:34].C(N(CC)CC)C>C(Cl)Cl>[O:30]=[C:31]([N:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([NH:7][C:8]2[CH:13]=[N:12][CH:11]=[C:10]([C:14]3[CH:15]=[N:16][N:17]4[CH:22]=[CH:21][N:20]=[CH:19][C:18]=34)[N:9]=2)[CH2:2]1)[CH2:32][C:33]#[N:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 534158962,5-Dioxopyrrolidin-1-yl 2-cyanoacetateHCID 66670500HCID 66670500, compound

Product 1

HCID 53373668HCID 53373668, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)—N-(piperidin-3-yl)-6-(pyrazolo[1,5-a]pyrazin-3-yl)pyrazin-2-amine (Preparation 30b, 0.23 g, 0.78 mmol), 3-[(2,5-dioxopyrrolidin-1-yl)oxy]-3-oxopropane nitrile (prepared as described in BE875054(A1), 0.17 g, 0.94 mmol)) and triethylamine (0.13 mL, 0.94 mmol) in methylene chloride (10 mL) was stirred overnight at ambient temperature. After evaporation of the solvent, the crude mixture was purified by flash chromatography (95:5 to 93:7 methylene chloride/methanol) to yield the title compound (0.158 g, 38%) as a pale yellow solid.

Workup

  1. customAfter evaporation of the solvent
  2. customthe crude mixture was purified by flash chromatography (95:5 to 93:7 methylene chloride/methanol)

Sources & evidence

ORD record
ord-eb06509d5cd34af2af92c2a71c671951
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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