Hydrochloric Acid → HCID 66674206, compound

HRID 423149Notes

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>C(OC(=O)C)CCC>[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 n-butylacetate (92 ml; Example 8) was added ethanol (235.3 ml) followed by n-butylacetate (117.7 ml) and the solution was heated to 60° C. Seed (0.1 g) was added to the hot solution followed by a solution of hydrochloric acid in isopropanol (13.44 ml, 4.68M, 62.9 mol) and the solution cooled to −10° C. over 10 hrs. The crystals were filtered and washed twice with ethanol (20 ml). After drying at 40° C. under vacuum gave 21.46 g, 79% yield of (5-Cyano-2-nitro-phenyl)-(5-morpholin-4-ylmethyl-pyridin-2-yl)-acetic acid ethyl ester hydrochloride salt as red wine crystals. Characterisation data were in accordance with example 7.

Workup

additionSeed (0.1 g) was added to the hot solution
temperaturethe solution cooled to −10° C. over 10 hrs
filtrationThe crystals were filtered
washwashed twice with ethanol (20 ml)
customAfter drying at 40° C. under vacuum

Sources & evidence

ORD record: ord-ad4a707d25d6412eb39ec3243ead09c3
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101750B2

Reaction notes

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