Dimethylformamide → HCID 58869148, compound

HRID 2355222Notes

Reaction equation

HRID 2355222 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH2:15][CH2:16][C@H:17]([CH2:21][NH:22][CH3:23])[O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH2:24](N(CC)CC)C.C[N:32]([CH:34]=[O:35])C>>[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH2:15][CH2:16][C@H:17]([CH2:21][N:22]([CH3:24])[CH2:23][C:34]([NH2:32])=[O:35])[O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 16225761HCID 16225761, compound

Product 1

HCID 58869148HCID 58869148, compound

Conditions

Temperature
60 °C

Procedure

To a solution of [(R)-7-(3-fluoro-benzenesulfonyl)-chroman-2-ylmethyl]-methyl-amine (0.08 g, 0.2.8 mmol) in dry DMF (2 mL) was added triethylamine (0.1 mL, 0.72 mmol) and 3-bromoacetamide (0.32 g, 0.24 mmol). The reaction mixture was stirred for six hours at 60° C., then cooled and quenched by addition of water. The reaction mixture was extracted with diethyl ether, and the combined organic layers were washed with water and brine, dried (MgSO4), filtered and contrated under reduced pressure. Purification of the residue by flash chromatography (MeOH/methylene chloride 1/4) gave 0.08 g of 2-{[(R)-7-(3-fluoro-benzenesulfonyl)-chroman-2-ylmethyl]-methyl-amino}-acetamide as a foam. MS (M+H)=393.

Workup

  1. temperaturecooled
  2. customquenched by addition of water
  3. extractionThe reaction mixture was extracted with diethyl ether
  4. washthe combined organic layers were washed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customPurification of the residue by flash chromatography (MeOH/methylene chloride 1/4)

Sources & evidence

ORD record
ord-edd639813a3f405ea47097ddc3972b2a
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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