Dimethylacetamide → HCID 24983317, compound

HRID 1676264Notes

Reaction equation

HRID 1676264 reaction equation
[CH2:1]([N:3]([CH2:25][CH3:26])[CH2:4][C:5]#[C:6][C:7]1[S:15][C:14]2[C:9](=[N:10][CH:11]=[CH:12][C:13]=2[O:16][C:17]2[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][C:18]=2[F:24])[CH:8]=1)[CH3:2].[CH3:27][C:28](N(C)C)=[O:29]>>[CH2:25]([N:3]([CH2:1][CH3:2])[CH2:4][C:5]#[C:6][C:7]1[S:15][C:14]2[C:9](=[N:10][CH:11]=[CH:12][C:13]=2[O:16][C:17]2[CH:23]=[CH:22][C:20]([NH:21][C:28](=[O:29])[CH3:27])=[CH:19][C:18]=2[F:24])[CH:8]=1)[CH3:26]

Participants

3

Reactant 2

HCID 31374DimethylacetamideHCID 67346706HCID 67346706, compound

Product 1

HCID 24983317HCID 24983317, compound

Conditions

Temperature
100 °C

Procedure

A 20 mL scintillation vial was charged with polystyrene-2,3,5,6-tetrafluoro-4-(methylcarbamoyl)phenyl acetate (0.179 g, 0.238 mmol). 4-(2-(3-(Diethylamino)-prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamine (Example 6, Step B 0.022 g, 0.0595 mmol) in DMA (2 mL) was added to the resin, and the mixture was heated at 100° C. with shaking for 96 hours. The reaction was cooled to room temperature and filtered using a vacuum master and Jones tubes. The filtrate was collected in 13 mm test tubes. The resin was washed with DMA (2 mL) making the total volume 4 mL. The crude material was dried using a GeneVac DD-4 set at 50° C. for the chamber and vial holder. Vacuum was set to aqua speed and reached a pressure of 7 mm Hg. The crude oil was purified by reverse phase chromatography (see purification method A, below). The final product was a TFA salt and a yellow oil (6.9 mg, 16%). Final Purity: 97%, LRMS (APCI pos) m/e 412.1 (M+1).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered
  3. customThe filtrate was collected in 13 mm test tubes
  4. washThe resin was washed with DMA (2 mL)
  5. dry with materialThe crude material was dried
  6. customset at 50° C. for the chamber and vial holder
  7. customThe crude oil was purified by reverse phase chromatography (see purification method A, below)

Sources & evidence

ORD record
ord-d48be00577944e4d974557bd0abfc5ce
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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