Hydrochloric Acid → HCID 66674206, compound

HRID 423148Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:30])[CH:5]([C:19]1[CH:24]=[C:23]([C:25]#[N:26])[CH:22]=[CH:21][C:20]=1[N+:27]([O-:29])=[O:28])[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:8][N:7]=1)[CH3:2].C(O)C.[ClH:34].C(O)(C)C>C1(C)C=CC=CC=1>[ClH:34].[CH2:1]([O:3][C:4](=[O:30])[CH:5]([C:19]1[CH:24]=[C:23]([C:25]#[N:26])[CH:22]=[CH:21][C:20]=1[N+:27]([O-:29])=[O:28])[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)=[CH:8][N:7]=1)[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To the (5-Cyano-2-nitro-phenyl)-(5-morpholin-4-ylmethyl-pyridin-2-yl)-acetic acid ethyl ester solution in toluene (196 ml; Example 7) was added ethanol (394 ml) and the solution is heated to 60° C. A solution of hydrochloric acid in isopropanol (26.8 ml, 4.87M, 103.3 mol) was then added followed by addition of seeds (317 mg) and the solution cooled to −10° C. over 10 hrs. The crystals were filtered and washed three times with ethanol (63 ml). After drying at 40° C. under vacuum gave 48.62 g, 87% yield of (5-Cyano-2-nitro-phenyl)-(5-morpholin-4-ylmethyl-pyridin-2-yl)-acetic acid ethyl ester hydrochloride salt as red wine crystals.

Workup

additionfollowed by addition of seeds (317 mg)
temperaturethe solution cooled to −10° C. over 10 hrs
filtrationThe crystals were filtered
washwashed three times with ethanol (63 ml)
customAfter drying at 40° C. under vacuum

Sources & evidence

ORD record: ord-142509bd808c4fdda0cd086abff2e820
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101750B2

Reaction notes

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