Dimethyl Sulfoxide → HCID 69017210, compound

HRID 491674Notes

Reaction equation

HRID 491674 reaction equation
[CH2:1]([O:8][C:9]1[CH:22]=[CH:21][C:12]([O:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16](Cl)[CH:15]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(C)=O.C[CH2:28][N:29](C(C)C)C(C)C.CN>C1COCC1>[CH2:1]([O:8][C:9]1[CH:22]=[CH:21][C:12]([O:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH:29][CH3:28])[CH:15]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6329Methylamine2×HCID 81531DiisopropylethylamineHCID 77231474HCID 77231474, compound

Product 1

HCID 69017210HCID 69017210, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

In a 350 mL sealed tube fitted with stirring bar were combined at 0° C. 4-(4-benzyloxy-phenoxy)-2-chloro-pyridine (Step a, 2.11 g, 6.79 mmol), DMSO (10 mL), DIEA (1.3 mL, 7.47 mmol), and CH3NH2 (4.1 mL of a 2 N solution in THF, 8.15 mmol). The reaction was heated to 100° C. for 7 days. During that period, an additional amount of CH3NH2 solution was added on four separate days (for a total of 70 mL). The reaction was cooled to RT and diluted into 1N NaOH and Et2O after evaporating off THF. After separation of the layers, the organic layer was washed 3× with 1 N NaOH then with brine. The crude residue was eluted on a silica gel column with a hexanes/EtOAc gradient to yield the title compound.

Workup

  1. customIn a 350 mL sealed tube
  2. customfitted
  3. customwere combined at 0° C
  4. waitDuring that period
  5. customseparate days (for a total of 70 mL)
  6. temperatureThe reaction was cooled to RT
  7. additiondiluted into 1N NaOH and Et2O
  8. customafter evaporating off THF
  9. customAfter separation of the layers
  10. washthe organic layer was washed 3× with 1 N NaOH
  11. washThe crude residue was eluted on a silica gel column with a hexanes/EtOAc gradient

Sources & evidence

ORD record
ord-f901919aabae4ffca6719a1f377276bd
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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