Tert-butyl 4-formylbenzoate → HCID 178450684, compound

HRID 1486570Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:14]=[C:13]([NH2:15])[NH:12][N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:16]([O:20][C:21](=[O:30])[C:22]1[CH:27]=[CH:26][C:25]([CH:28]=O)=[CH:24][CH:23]=1)([CH3:19])([CH3:18])[CH3:17].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:14]=[C:13]([NH:15][CH2:28][C:25]3[CH:26]=[CH:27][C:22]([C:21]([O:20][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:30])=[CH:23][CH:24]=3)[NH:12][N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of N3-(3,5-dichlorophenyl)-1H-1,2,4-triazole-3,5-diamine Intermediate 3 (70 mg, 287 μmol) and 4-formyl-benzoic acid mono tert-butyl ester (150 mg, 727 μmol) in MeOH (3 ml) was stirred at 45° C. for overnight to give a suspension, cooled to −20° C. and was filtered to collect the solid. The solid was re-suspended in MeOH (5 ml), NaBH4 (65.1 mg, 1.72 mmol) was added and the reaction was stirred for 1 hour. The solvent was removed, and the reaction mixture was redissolved in EtOAc (5 ml) and washed with water (2×4 ml), dried over MgSO4 and concentrated in vacuo. Crystallization from EtOAc/hexanes afforded a white solid as desired product (116 mg, 93% yield). MS +m/z: 434 (M+H)+

Workup

customto give a suspension
filtrationwas filtered
customto collect the solid
customThe solvent was removed
dissolutionthe reaction mixture was redissolved in EtOAc (5 ml)
washwashed with water (2×4 ml)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customCrystallization from EtOAc/hexanes

Sources & evidence

ORD record: ord-1375f1f2a3ea4b22a7a1d48215690faa
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428469B2

Reaction notes

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