HCID 67776061, compound → HCID 67776316, compound

HRID 63530Notes

Reaction equation

HRID 63530 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]([NH:19][CH3:20])=[O:18])=[C:15]3[C:10]([CH:11]=[C:12]([N+:24]([O-])=O)[C:13]([CH:21]4[CH2:23][CH2:22]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1>C1COCC1.CO.[Ni]>[NH2:24][C:12]1[C:13]([CH:21]2[CH2:23][CH2:22]2)=[CH:14][C:15]2[C:10]([CH:11]=1)=[N:9][N:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C:16]=2[C:17]([NH:19][CH3:20])=[O:18]

Participants

5

Reactant 1

HCID 67776061HCID 67776061, compound

Product 1

HCID 67776316HCID 67776316, compoundYield 83.7%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (vii) (127 mg, 0.34 mmol) in THF (2.5 mL) and MeOH (7.5 mL) was added Raney nickel (20 mg) and the reaction stirred vigorously under hydrogen atmosphere at 60° C. for 2 h. The reaction was diluted with MeOH (40 mL), filtered and then concentrated to dryness to give (viii) (97 mg, 83%). ESI-MS m/z calculated for [M+H]+: 341.1. found: 341.0. 1H NMR (400 MHz, d6-DMSO) δ 7.58-7.47 (m, 4H), 7.23 (s, 1H), 6.64 (m, 1H), 2.85-2.76 (m, 3H), 1.82-1.72 (m, 1H), 0.96-0.89 (m, 2H), 0.64-0.55 (m, 2H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-81e26543d470461ea6a61ea16b3b92b8
Source dataset
uspto-grants-2016_09
Patent number
US09447080B2

Reaction notes

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