1,1'-Carbonyldiimidazole → N'-boc-3-(3-(2-chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl)-4-methylbenzohydrazide

HRID 643674Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]2[CH:13]=[CH:14][C:15]([C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=3[CH3:26])[C:20](O)=[O:21])=[CH:16][C:11]2=[N:10][N:9]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[C:39]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])(=[O:42])[NH:40][NH2:41]>C1COCC1>[C:39]([NH:40][NH:41][C:20](=[O:21])[C:19]1[CH:23]=[CH:24][C:25]([CH3:26])=[C:17]([C:15]2[CH:14]=[CH:13][N:12]3[C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])=[N:9][N:10]=[C:11]3[CH:16]=2)[CH:18]=1)([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 3-(3-(2-chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl)-4-methylbenzoic acid (444 mg, 1.22 mmol) in 15 mL of THF at RT was added CDI (218 mg, 1.34 mmol). The resulting mixture was heated for 1 h at 50° C. The reaction mixture was then cooled to RT and tert-butyl carbazate (177 mg, 1.34 mmol) was added. The reaction mixture was again heated at 50° C. for 24 h. After the reaction mixture was concentrated to dryness, the residue was purified on the ISCO (40 g column, 50-100% EtOAc in Hexanes) to afford the title compound as an off-white amorphous solid. MS (ESI, pos. ion) m/z: 478.1 (M+1).

Workup

temperatureThe reaction mixture was then cooled to RT
temperatureThe reaction mixture was again heated at 50° C. for 24 h
concentrationAfter the reaction mixture was concentrated to dryness
customthe residue was purified on the ISCO (40 g column, 50-100% EtOAc in Hexanes)

Sources & evidence

ORD record: ord-3133468e29974676a713f41669bf29ea
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700593B2

Reaction notes

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