Triethylamine → HCID 66576683, compound

HRID 1409408Notes

Reaction equation

HRID 1409408 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8](Cl)=[O:9])=[N:6][CH:7]=1.C(N(CC)CC)C.[NH2:18][C@@H:19]([CH3:35])[CH2:20][N:21]1[CH:25]=[CH:24][C:23]([C:26]2[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[C:28]([Cl:34])[CH:27]=2)=[N:22]1>C1COCC1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([NH:18][C@@H:19]([CH3:35])[CH2:20][N:21]2[CH:25]=[CH:24][C:23]([C:26]3[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[C:28]([Cl:34])[CH:27]=3)=[N:22]2)=[O:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 152157435-Chloropyrazine-2-carbonyl chlorideHCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Product 1

HCID 66576683HCID 66576683, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Chloropyrazine-2-carbonyl chloride (3.28 mmol, 580 mg) was dissolved in dry THF (40 ml). Triethylamine (9.83 mmol, 995 mg) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (3.28 mmol, 854 mg) were added and the resulting mixture was stirred for one day at RT. The crude product was purified by recrystallization from DCM. 900 mg of the title compound was obtained. 1H-NMR (400 MHz, CDCl3): δ 1.25 (d, 3H), 4.29 (dd, 1H), 4.47 (dd, 1H), 4.59-4.71 (m, 1H), 6.66 (d, 1H), 7.51 (d, 1H), 7.68-7.73 (m, 1H), 7.75-7.80 (m, 1H), 8.12 (d, 1H), 8.64 (d, 1H), 8.77 (d, 1H), 9.17 (d, 1H).

Workup

  1. customThe crude product was purified by recrystallization from DCM

Sources & evidence

ORD record
ord-5612afc5a05c43eb934132b0cc73257e
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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