Pyridine → HCID 86267636, compound

HRID 1049320Notes

Reaction equation

HRID 1049320 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:15]=[CH:16][C:17]([NH:20][C:21]([NH:23][C:24](=[O:32])[CH2:25][CH:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=[O:22])=[N:18][CH:19]=3)[CH:10]=[CH:9][N:8]=2)[CH:4]=[N:3]1.N1C=CC=C[CH:34]=1.C1COCC1>ClCCCl>[CH3:34][C:19]1[N:18]=[C:17]([NH:20][C:21]([NH:23][C:24](=[O:32])[CH2:25][CH:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[O:22])[CH:16]=[CH:15][C:14]=1[O:13][C:11]1[CH:10]=[CH:9][N:8]=[C:7]([C:5]2[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 86267431HCID 86267431, compound

Product 1

HCID 86267636HCID 86267636, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of crude 2-(tetrahydro-2H-pyran-4-yl)acetyl isocyanate (0.110 g, 0.650 mmol, see Example 4) in DCE (7 mL) was treated with Example A6 (0.183 g, 0.650 mmol) and stirred at RT overnight. Pyridine (0.11 mL, 1.3 mmol) was added, the mixture stirred at RT for 4 h, treated with THF, then washed with satd. NaHCO3 and brine, dried over MgSO4 and concentrated to dryness. The resulting material was treated with MeCN, and the solid collected via filtration and dried to afford N-((6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)-2-(tetrahydro-2H-pyran-4-yl)acetamide (56 mg, 19%) as a pale tan solid. MS (ESI) m/z: 451.2 (M+H+).

Workup

  1. stirringthe mixture stirred at RT for 4 h
  2. washwashed with satd
  3. dry with materialNaHCO3 and brine, dried over MgSO4
  4. concentrationconcentrated to dryness
  5. additionThe resulting material was treated with MeCN
  6. filtrationthe solid collected via filtration
  7. customdried

Sources & evidence

ORD record
ord-2ab90126302543fc8035f92a0bb59c83
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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