HCID 46186185, compound → HCID 46186186, compound

HRID 341285Notes

Reaction equation

HRID 341285 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([CH2:19][CH2:20][N+:21]([O-])=O)=[CH:16][CH:17]=3)[C:12]3[CH:24]=[C:25]([Cl:28])[CH:26]=[N:27][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.[Ni]>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([CH2:19][CH2:20][NH2:21])=[CH:16][CH:17]=3)[C:12]3[CH:24]=[C:25]([Cl:28])[CH:26]=[N:27][C:11]2=3)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 46186185HCID 46186185, compound

Product 1

HCID 46186186HCID 46186186, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 15 (72 mg, 0.17 mmol) in MeOH (1 mL) was added a catalytic amount of Ni Raney. This mixture was stirred overnight at 50° C. under nitrogen atmosphere. The solids were filtered off and the filtrate evaporated to give 16. 1H-NMR (300 MHz, DMSO-d6): δ 8.78 (d, 1H, J=2.4 Hz), 8.60 (d, 1H, J=2.4 Hz), 8.30 (d, 1H, J=8.7 Hz), 8.14 (bs, 1H), 8.04 (d, 1H, J=8.7 Hz); 8.02 (d, 1H, J=7.2 Hz), 7.70 (t, 1H, J=7.2 Hz), 7.59-7.54 (m, 3H), 6.74 (bs, 2H); 3.05 (m, 2H), 2.96 (m, 2H); MS (ESI) m/z 386 [M-NH3+], 386 [M+H+], 408 [M+Na+].

Workup

  1. filtrationThe solids were filtered off
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-21463cc28afb45129c33416c1eafacff
Source dataset
uspto-grants-2014_11
Patent number
US08895744B2

Reaction notes

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