Borohydride → HCID 66918852, compound

HRID 2354231Notes

Reaction equation

HRID 2354231 reaction equation
[BH4-].[CH:2]1([NH:5][C:6](=[O:26])[C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([NH:14][C:15](=[O:25])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N+:22]([O-])=O)[CH:8]=2)[CH2:4][CH2:3]1>CO.O.O.O.O.C([O-])(=O)C.[Ni+2].C([O-])(=O)C.[Au]>[NH2:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:15]([NH:14][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[CH3:13])[C:6]([NH:5][CH:2]1[CH2:4][CH2:3]1)=[O:26])=[O:25]

Participants

6

Reactant 2

HCID 28123BorohydrideHCID 66918762HCID 66918762, compound

Product 1

HCID 66918852HCID 66918852, compoundYield 11.5%

Reagents, catalysts & solvents 3

HCID 23985GoldCatalystHCID 62601Nickel acetate tetrahydrateCatalystHCID 887MethanolSolvent

Procedure

Nickel acetate tetrahydrate (0.119 g) was added to a suspension of Borohydride on Amerlite IRA-400 resin (8.96 g) in methanol (90 ml). Gas was evolved and the resin turned from a light gold to black. After 1 minute the N-cyclopropyl-4-methyl-3-[(2-nitrobenzoyl)amino]benzamide (1.52 g) was added in a single portion and the mixture stirred at room temperature. After 1 hour the reaction was filtered through diatomaceous earth (Celite®) and the filtrate concentrated onto silica gel (2.0 g). Purification by column chromatography (isolute silica 50 g column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK) using a gradient of 0% iso-propanol/iso-hexane through to 50% iso-propanol/iso-hexane to give 3-[(2-aminobenzoyl)amino]-N-cyclopropyl-4-methylbenzamide as a white solid (0.159 g); NMR Spectrum: (DMSOd6) 0.58 (m, 2H), 0.69 (m, 2H), 2.26 (s, 3H), 2.85 (m, 1H), 6.40 (s, 2H), 6.59 (t, 1H), 6.76 (d, 1H), 7.21 (t, 1H), 7.33 (d, 1H), 7.63 (m, 1H), 7.72 (d, 1H), 7.78 (d, 1H), 8.36 (d, 1H), 9.70 (d, 1H); Mass Spectrum: M+H+ 310.

Workup

  1. filtrationAfter 1 hour the reaction was filtered through diatomaceous earth (Celite®)
  2. concentrationthe filtrate concentrated onto silica gel (2.0 g)
  3. customPurification by column chromatography (isolute silica 50 g column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK)

Sources & evidence

ORD record
ord-328fa45135c843e69c32ef30c97f5e6b
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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