Dimethylformamide → HCID 44430464, compound

HRID 1984321Notes

Reaction equation

HRID 1984321 reaction equation
[N:1]1([C:8]2[N:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)C=[C:10]([N:17]3[CH2:20][CH:19](OS(C)(=O)=O)[CH2:18]3)[C:9]=2[CH3:26])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br-:27].[Na+].C[N:30](C)C=O>>[Br:27][CH:19]1[CH2:20][N:17]([C:10]2[N:30]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[N:13]=[C:8]([N:1]3[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[C:9]=2[CH3:26])[CH2:18]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 253881Sodium BromideHCID 86604161HCID 86604161, compound

Product 1

HCID 44430464HCID 44430464, compoundYield 30%

Conditions

Temperature
100 °C

Procedure

A mixture of methanesulfonic acid 1-(6-azepan-1-yl-2-cyclopropyl-5-methyl-pyridin-4-yl)-azetidin-3-yl ester 190 (0.4 g, 1 mmol) and sodium bromide (0.103 g, 1 mmol) in N,N-dimethylformamide (10 ml) is heated at 100° C. for 6 days. The mixture is then cooled and concentrated in vacuo. The mixture is diluted with dichloromethane and washed two times with water. The combined organic layers are dried over magnesium sulfate and concentrated in vacuo to afford 0.4 g of a crude mixture, which is purified by column chromatography (dichloromethane/methanol 98/2). 1-[6-(3-bromo-azetidin-1-yl)-2-cyclopropyl-5-methyl-pyrimidin-4-yl]-azepane 182 (0.11 g, 30%) is obtained.

Workup

  1. temperatureThe mixture is then cooled
  2. concentrationconcentrated in vacuo
  3. additionThe mixture is diluted with dichloromethane
  4. washwashed two times with water
  5. dry with materialThe combined organic layers are dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto afford 0.4 g of a crude mixture, which
  8. customis purified by column chromatography (dichloromethane/methanol 98/2)

Sources & evidence

ORD record
ord-af097079104d45939befc49fca1deff9
Source dataset
uspto-grants-2009_06
Patent number
US07544675B2

Reaction notes

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