HCID 21913507, compound → HCID 69193218, compound

HRID 1352600Notes

Reaction equation

HRID 1352600 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([NH:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][C:16]2[S:17][CH:18]=[CH:19][N:20]=2)[C:5]([N+:21]([O-])=O)=[C:4]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:3]=1>C1(C)C=CC=CC=1>[CH3:8][C:7]1[C:6]([NH:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][C:16]2[S:17][CH:18]=[CH:19][N:20]=2)=[C:5]([NH2:21])[C:4]([O:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[N:3][C:2]=1[CH3:1]

Participants

3

Reactant 1

HCID 21913507HCID 21913507, compound

Product 1

HCID 69193218HCID 69193218, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a nitrogen purge, 5% platinum on carbon (0.5 g) and toluene (5 mL) were added to a pressure vessel. A solution of (2,3-dimethyl-5-nitro-6-phenoxypyridin-4-yl)-{2-[3-(1,3-thiazol-2-yl)propoxy]ethyl}amine (4.7 g, 11 mmol) in toluene (35 mL) was then added. The vessel was placed under hydrogen pressure (50 psi, 3.4×105 Pa) for 24 hours. The reaction mixture was filtered through a layer of CELITE filter aid, and the filtrate was concentrated under reduced pressure to yield 4.12 g of 5,6-dimethyl-2-phenoxy-N4-{2-[3-(1,3-thiazol-2-yl)propoxy]ethyl}pyridine-3,4-diamine as a pale yellow oil.

Workup

  1. customUnder a nitrogen purge
  2. addition5% platinum on carbon (0.5 g) and toluene (5 mL) were added to a pressure vessel
  3. customfor 24 hours
  4. filtrationThe reaction mixture was filtered through a layer of CELITE
  5. filtrationfilter aid
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-939f4b1115f146a2b982fa5f1eef3435
Source dataset
uspto-grants-2007_05
Patent number
US07220758B2

Reaction notes

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