HCID 67457507, compound → HCID 49771654, compound

HRID 639610Notes

Reaction equation

HRID 639610 reaction equation
C(O[C:4](=[O:30])[N:5]([C:13]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])[N:16]=[C:15]([NH2:26])[C:14]=1[N+:27]([O-])=O)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C>C(O)(=O)C.CO.[Zn]>[NH2:26][C:15]1[C:14]2[NH:27][C:4](=[O:30])[N:5]([CH2:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:13]=2[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])[N:16]=1

Participants

5

Reactant 1

HCID 67457507HCID 67457507, compound

Product 1

HCID 49771654HCID 49771654, compoundYield 31.7%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

[2-Amino-6-(2-fluoro-phenyl)-3-nitro-pyridin-4-yl]-benzyl-carbamic acid ethyl ester (31 mg) was dissolved in acetic acid (1 ml). Zinc powder (Aldrich, 99%, 20 mg) was added and the mixture left to stir at room temperature under nitrogen for 2 hours. Additional zinc powder (30 mg) was added and mixture left to stir for a further 1 hour. The reaction mixture was diluted with methanol (2 ml) then filtered directly onto a cation exchange cartridge (Bakerbond SCX, sulphonic acid bonded-phase, 1 g). The SCX cartridge was washed with methanol (2×5 ml) to remove impurities and then the product was released with ammonia in methanol (2 M, 5 ml). The desired fraction was evaporated to a pale brown solid. This was triturated with ethyl acetate then filtered and washed with more ethyl acetate to yield the title compound (8 mg) as a pale purple solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.99 (s, 2 H) 5.82 (s, 2 H) 6.87 (d, J=1.95 Hz, 1 H) 7.15-7.29 (m, 3 H) 7.29-7.39 (m, 5 H) 7.81 (td, J=8.01, 1.95 Hz, 1 H) 10.51 (s, 1 H), LCMS Rt=2.21 m/z 335 [MH]+

Workup

  1. waitthe mixture left
  2. waitmixture left
  3. stirringto stir for a further 1 hour
  4. filtrationthen filtered directly onto a cation exchange cartridge (Bakerbond SCX, sulphonic acid bonded-phase, 1 g)
  5. washThe SCX cartridge was washed with methanol (2×5 ml)
  6. customto remove impurities
  7. customThe desired fraction was evaporated to a pale brown solid
  8. customThis was triturated with ethyl acetate
  9. filtrationthen filtered
  10. washwashed with more ethyl acetate

Sources & evidence

ORD record
ord-dba141a8f31b4a75a3343c200ca01d4d
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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