Dimethylformamide → HCID 11611268, compound

HRID 550429Notes

Reaction equation

HRID 550429 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[N:22]=[CH:21][N:20]=[C:19]3[NH:23][N:24]=[C:25]([O:26][CH2:27][CH2:28]O)[C:18]=23)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1.CN(C=O)C.S(Cl)([Cl:37])=O>>[Cl:37][CH2:28][CH2:27][O:26][C:25]1[C:18]2[C:19](=[N:20][CH:21]=[N:22][C:17]=2[NH:16][C:4]2[CH:5]=[CH:6][C:7]([O:8][C:9]3[CH:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=3)=[C:2]([CH3:1])[CH:3]=2)[NH:23][N:24]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 67020769HCID 67020769, compound

Product 1

HCID 11611268HCID 11611268, compoundYield 84%

Procedure

2-{[4-({3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}amino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]oxy}ethanol (prepared as described in Example 8/1.7 g, 4.33 mmol) was dissolved in thionyl chloride (10 ml) and DMF (100 μL) was added. The mixture was refluxed for 2 hours and then the volatiles were removed under reduced pressure. The residue was triturated with a saturated solution of sodium bicarbonate and the solid filtered and washed with ether to provide the title compound (1.5 g, 84%); NMR Spectrum: 2.20 (s, 3H), 2.44 (s, 3H), 4.09 (t, 2H), 4.60 (t, 2H), 6.96 (d, 1H), 7.18-7.25 (m, 2H), 7.60 (d, 1H), 7.67 (s, 1H), 8.17 (s, 1H), 8.31 (s, 1H), 8.34 (br s, 1H); Mass Spectrum: 411 (MH+).

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. customthe volatiles were removed under reduced pressure
  3. customThe residue was triturated with a saturated solution of sodium bicarbonate
  4. filtrationthe solid filtered
  5. washwashed with ether

Sources & evidence

ORD record
ord-e09cf0ff891b43448e241aa7171fb0b1
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

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