1,4-Dioxane hydrochloride → HCID 67498956, compound

HRID 1484730Notes

Reaction equation

[Cl:1][C:2]1[C:6]([N:7]([CH2:15][CH3:16])C(=O)OC(C)(C)C)=[CH:5][N:4]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[N:3]=1.Cl.O1CCOCC1>O1CCOCC1>[ClH:1].[Cl:1][C:2]1[C:6]([NH:7][CH2:15][CH3:16])=[CH:5][N:4]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[N:3]=1

Participants

Conditions

Temperature: 1 °C

Procedure

Into a 500 mL three-necked round bottom flask equipped with a magnetic stir bar was added a solution of tert-butyl (3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)(ethyl)carbamate (21 g, 65.1 mmol) in 1.4-dioxane (35 mL). This pale yellow solution was placed into an ice bath and cooled to 1° C. A solution of 4M HCl/dioxane (65 mL, 260 mmol) was added in one portion. After stirring for 20 minutes, the ice bath was removed and the suspension was stirred further at ambient temperature for 16 hours. The reaction was diluted with 200 mL of ethyl ether and the solid was filtered and washed with ether and placed in a vacuum oven at 40° C. for 18 hours. The title compound was isolated as a pale yellow solid (18.2 g, 95%): 1H NMR (400 MHz, MeOD) δ 9.52 (d, J=2.5 Hz, 1H), 9.17 (s, 1H), 9.14 (ddd, J=8.7, 2.5, 1.1 Hz, 1H), 8.93 (ddd, J=5.7, 1.1, 0.6 Hz, 1H), 8.31 (ddd, J=8.7, 5.7, 0.5 Hz, 1H), 3.58 (q, J=7.3 Hz, 2H), 1.48 (t, J=7.3 Hz, 3H); ESIMS m/z 223 ([M+H]+).

Workup

customInto a 500 mL three-necked round bottom flask equipped with a magnetic stir bar
customThis pale yellow solution was placed into an ice bath
customthe ice bath was removed
stirringthe suspension was stirred further at ambient temperature for 16 hours
additionThe reaction was diluted with 200 mL of ethyl ether
filtrationthe solid was filtered
washwashed with ether
waitplaced in a vacuum oven at 40° C. for 18 hours

Sources & evidence

ORD record: ord-5f83fbc0e402440c81c9eea85a6f7d6a
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422278B2

Reaction notes

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