Sodium borohydride → HCID 178452735, compound

HRID 1486569Notes

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.[CH:16]([C:18]1[CH:19]=[CH:20][C:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[N:22][CH:23]=1)=O.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:14]=[C:13]([NH:15][CH2:16][C:18]3[CH:19]=[CH:20][C:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[N:22][CH:23]=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 2 (70 mg, 287 μmol) and tert-butyl (5-formylpyridine-2-yl)carbamate (159 mg, 717 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 (163 mg, 4.3 mmol) was added in a few portions 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. Purification by flash chromatography (silica gel, 24 g, 3% to 6% MeOH in DCM) afforded a white solid as desired product (60.8 mg, 47% yield). MS +m/z: 450 (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
customPurification by flash chromatography (silica gel, 24 g, 3% to 6% MeOH in DCM)

Sources & evidence

ORD record: ord-6760b5efa3f541b7866c7e6772304466
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428469B2

Reaction notes

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