Pyridine → HCID 69306513, compound

HRID 2056767Notes

Reaction equation

HRID 2056767 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C@H:20]3[C:25]4[CH:26]=[CH:27][C:28]([NH2:30])=[CH:29][C:24]=4[CH2:23][CH2:22][O:21]3)[C@@H:14]([CH3:31])[CH2:13]1)=[CH:7][CH:6]=[CH:5]2.N1C=CC=CC=1.Cl[C:39]([O:41][CH2:42][CH2:43]Cl)=[O:40]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C@H:20]3[C:25]4[CH:26]=[CH:27][C:28]([N:30]5[CH2:43][CH2:42][O:41][C:39]5=[O:40])=[CH:29][C:24]=4[CH2:23][CH2:22][O:21]3)[C@H:14]([CH3:31])[CH2:13]1)=[CH:7][CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 123052-Chloroethyl chloroformateHCID 69306548HCID 69306548, compound

Product 1

HCID 69306513HCID 69306513, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1S)-1-{2-[(2S)-4-(6-fluoro-1-naphthyl)-2-methyl-piperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-amine (0.217 g, mmol) in dry DMF (5 mL) was added pyridine (0.05 mL, mmol) and 2-chloroethyl chloroformate (0.055 mL, mmol), and the reaction stirred at room temperature under nitrogen for 2 h. The reaction was quenched by addition of 2M sodium hydroxide (3 mL), diluted with water and extracted into dichloromethane. The combined organic extracts were dried (MgSO4), filtered and evaporated in vacuo. The crude product was purified by prep LCMS to yield 3-((1S)-1-{2-[(2R)-4-(6-fluoro-1-naphthyl)-2-methylpiperazinyl]-ethyl}-3,4-dihydro-1H-2-benzopyran-6-yl)-1,3-oxazolidin-2-one. M+H=490.

Workup

  1. customThe reaction was quenched by addition of 2M sodium hydroxide (3 mL)
  2. additiondiluted with water
  3. extractionextracted into dichloromethane
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe crude product was purified by prep LCMS

Sources & evidence

ORD record
ord-bc41727bbd5c4d7eaa9940fedbeb2cc1
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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