Ethyl 2-chloroethanecarboximidate hydrochloride → HCID 66957882, compound

HRID 1364077Notes

Reaction equation

[NH2:1][C:2]1[C:3]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:4][C:5]([CH3:21])=[C:6]([CH3:20])[C:7]=1[NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].Cl.[Cl:30][CH2:31][C:32](=N)OCC>C(Cl)(Cl)Cl>[Cl:30][CH2:31][C:32]1[N:8]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:7]2[C:6]([CH3:20])=[C:5]([CH3:21])[N:4]=[C:3]([O:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:2]=2[N:1]=1

Participants

Conditions

Temperature: 60 °C

Procedure

tert-Butyl 3-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]propylcarbamate (68.8 g, 178 mmol), prepared as described in U.S. Pat. No. 6,545,016, Example 17, Parts A through C, was dissolved in chloroform (600 mL). Ethyl 2-chloroacetimidate hydrochloride (56.0 g, 354 mmol) was added to the solution and the reaction mixture was stirred at 60° C. for 72 hours. The reaction mixture was diluted with chloroform (200 mL), washed with brine (2×600 mL), and the layers were separated. The combined organics were dried over magnesium sulfate, filtered through CELITE filter aid, and concentrated under reduced pressure to afford 91.62 g of tert-butyl 3-[2-(chloromethyl)-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]propylcarbamate.

Workup

washwashed with brine (2×600 mL)
customthe layers were separated
dry with materialThe combined organics were dried over magnesium sulfate
filtrationfiltered through CELITE
filtrationfilter aid
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-ba661bdab33b4c02933d9f590fea6437
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888349B2

Reaction notes

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