1,1'-Carbonyldiimidazole → [(3-Amino-pyridine-4-carbonyl)-amino]-acetic acid methyl ester

HRID 1887187Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:24][O:25][C:26](=[O:29])[CH2:27][NH2:28]>N1C=CC=CC=1>[CH3:24][O:25][C:26](=[O:29])[CH2:27][NH:28][C:4]([C:3]1[CH:7]=[CH:8][N:9]=[CH:10][C:2]=1[NH2:1])=[O:6]

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 100 mg of 3-amino-isonicotinic acid in pyridine (2.5 mL) is added 117 mg of 1,1′-carbonyldiimidazole and the mixture is stirred for 20 min at 55° C. Then the mixture is cooled to room temperature and 91 mg of glycine methylester hydrochloride is added and the resulting mixture is stirred for 30 min at 55° C. and 1 h at room temperature. Then the solvent is removed under vacuum and the residue is purified by flash chromatography on silica gel to give 100 mg (66%) of [(3-amino-pyridine-4-carbonyl)-amino]-acetic acid methyl ester.

Workup

temperatureThen the mixture is cooled to room temperature
stirringthe resulting mixture is stirred for 30 min at 55° C. and 1 h at room temperature
customThen the solvent is removed under vacuum
customthe residue is purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-148d16d125cf4e4d9e34182c2facaa08
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501749B2

Reaction notes

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