Water → HCID 69588473, compound

HRID 859158Notes

Reaction equation

HRID 859158 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][C:13]([SH:16])=[N:12][CH:11]=2)=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].CCN(C(C)C)C(C)C.O>CN(C=O)C>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][S:16][C:13]1[CH:14]=[CH:15][C:10]([C:9](=[O:17])[NH:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[C:3]([N+:18]([O-:20])=[O:19])[CH:4]=2)=[CH:11][N:12]=1)[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 178522152HCID 178522152, compound

Product 1

HCID 69588473HCID 69588473, compoundYield 107.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To mixture of the of N-(4-fluoro-3-nitrophenyl)-6-mercaptonicotinamide (200 mg, 0.68 mmol) and ethyl bromoacetate (113 μL, 1.02 mmol) in DMF (5 mL) was added DIPEA (243 μL, 1.4 mmol). The reaction mixture was stirred for 10 minutes before being poured into water and being extracted with ethyl acetate (3×50 mL). The combined extracts were washed with water and brine and were dried over magnesium sulfate. Filtration followed by concentration in vacuo gave 278 mg (100%) of [5-(4-fluoro-3-nitrophenylcarbamoyl)pyridin-2-ylsulfanyl]acetic acid ethyl ester as a solid: 1H NMR (300 MHz, acetone-d6) δ 10.0 (bs, 1H), 9.02 (m, 1H), 8.21 (m, 1H), 8.18 (m, 2H, 7.46 (m, 2H), 4.16 (m, 2H), 4.08 (s, 2H), 1.22 (m, 3H); MS (EI) m/z 377.88 (M−H)−.

Workup

  1. extractionbeing extracted with ethyl acetate (3×50 mL)
  2. washThe combined extracts were washed with water and brine
  3. dry with materialwere dried over magnesium sulfate
  4. filtrationFiltration
  5. concentrationfollowed by concentration in vacuo

Sources & evidence

ORD record
ord-c12d3d7f628c4b09bfbb0b09d0e81d34
Source dataset
uspto-grants-2006_12
Patent number
US07151112B1

Reaction notes

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