HCID 90403112, compound → HCID 90403028, compound

HRID 2278903Notes

Reaction equation

HRID 2278903 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:7]2[CH:12]=[C:11]([O:13][C:14]3[C:15]([CH3:23])=[N:16][C:17]([N+:20]([O-])=O)=[CH:18][CH:19]=3)[CH:10]=[CH:9][N:8]=2)=[CH:5][N:6]=1>CO.[Pd]>[CH3:23][C:15]1[N:16]=[C:17]([NH2:20])[CH:18]=[CH:19][C:14]=1[O:13][C:11]1[CH:10]=[CH:9][N:8]=[C:7]([C:4]2[S:3][C:2]([CH3:1])=[N:6][CH:5]=2)[CH:12]=1

Participants

4

Reactant 1

HCID 90403112HCID 90403112, compound

Product 1

HCID 90403028HCID 90403028, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

A solution of 2-methyl-5-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)thiazole (1.06 g, 3.23 mmol) in MeOH (40 mL) was treated with 10% Pd/C (50% w/w water, 0.344 g, 0.323 mmol) and hydrogenated (50 psi) overnight. Additional 10% Pd/C (50% w/w water, 0.344 g, 0.323 mmol) was added and the mixture hydrogenated (50 psi) for an additional 24 h. The solids were removed via filtration through diatomaceous earth, washed with MeOH and the filtrate concentrated to dryness. The material was treated with MTBE, the solid collected via filtration and dried to afford 6-methyl-5-((2-(2-methylthiazol-5-yl)pyridin-4-yl)oxy)pyridin-2-amine (860 mg, 89%). 1H NMR (400 MHz, DMSO-d6): δ 8.34 (d, J=5.8 Hz, 1 H), 8.28 (s, 1 H), 7.49 (d, J=2.4 Hz, 1 H), 7.19 (d, J=8.7 Hz, 1 H), 6.58 (dd, J=5.8, 2.4 Hz, 1 H), 6.35 (d, J=8.7 Hz, 1 H), 5.96 (s, 2 H), 2.65 (s, 3 H), 2.07 (s, 3 H); MS (ESI) m/z: 299.1 (M+H+).

Workup

  1. customThe solids were removed via filtration through diatomaceous earth
  2. washwashed with MeOH
  3. concentrationthe filtrate concentrated to dryness
  4. additionThe material was treated with MTBE
  5. filtrationthe solid collected via filtration
  6. customdried

Sources & evidence

ORD record
ord-3a501dbdcaca487280922e503ab8fa86
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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