HCID 86657733, compound → HCID 86657732, compound

HRID 1465673Notes

Reaction equation

HRID 1465673 reaction equation
[CH3:1][O:2][C:3]1[CH:34]=[CH:33][C:6]([O:7][C:8]2[CH:13]=[C:12]([CH3:14])[C:11]([C:15]3[N:16]=[C:17]([NH:20][C:21](=[O:31])[C:22]4[CH:27]=[CH:26][N:25]=[C:24]([N+:28]([O-])=O)[CH:23]=4)[S:18][CH:19]=3)=[C:10]([CH3:32])[CH:9]=2)=[CH:5][CH:4]=1>C(O)C.[Pd]>[NH2:28][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][N:25]=1)[C:21]([NH:20][C:17]1[S:18][CH:19]=[C:15]([C:11]2[C:10]([CH3:32])=[CH:9][C:8]([O:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:34][CH:33]=3)=[CH:13][C:12]=2[CH3:14])[N:16]=1)=[O:31]

Participants

4

Reactant 1

HCID 86657733HCID 86657733, compound

Product 1

HCID 86657732HCID 86657732, compoundYield 61.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-(4-(4-(4-methoxyphenoxy)-2,6-dimethylphenyl)thiazol-2-yl)-2-nitroisonicotinamide (0.20 g, 0.40 mmol) and Pd/C (0.15 g, 10% w/w) in ethanol (10 mL) was stirred under H2 overnight. The reaction was filtered through diatomaceous earth and concentrated under reduced pressure to provide 2-amino-N-(4-(4-(4-methoxyphenoxy)-2,6-dimethylphenyl)thiazol-2-yl)isonicotinamide (0.11 g) as yellow solids in 59% yield: 1H NMR (500 MHz, DMSO-d6) δ 7.88-7.89 (m, 1 H), 7.10-7.11 (m, 2 H), 6.95-6.97 (m, 2 H), 6.62 (s, 1 H), 5.76 (s, 1 H), 3.29 (s, 3 H), 2.03 (s, 6 H); ESI-MS: m/z 446.6 (M+H)+.

Workup

  1. filtrationThe reaction was filtered through diatomaceous earth
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e239e3e251b74399ac2d310e26f61761
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

Loading…