Ammonia → HCID 56598656, compound

HRID 72656Notes

Reaction equation

HRID 72656 reaction equation
[CH3:1][O:2][C:3]1[C:8]([NH:9][CH2:10][C:11](OCC)=[O:12])=[CH:7][C:6]([CH2:16][S:17](/[CH:20]=[CH:21]/[C:22]2[C:27]([O:28][CH3:29])=[CH:26][C:25]([O:30][CH3:31])=[CH:24][C:23]=2[O:32][CH3:33])(=[O:19])=[O:18])=[CH:5][N:4]=1.[NH3:34]>O>[CH3:1][O:2][C:3]1[C:8]([NH:9][CH2:10][C:11]([NH2:34])=[O:12])=[CH:7][C:6]([CH2:16][S:17](/[CH:20]=[CH:21]/[C:22]2[C:23]([O:32][CH3:33])=[CH:24][C:25]([O:30][CH3:31])=[CH:26][C:27]=2[O:28][CH3:29])(=[O:18])=[O:19])=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 56598518HCID 56598518, compound

Product 1

HCID 56598656HCID 56598656, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

(E)-ethyl 2-(2-methoxy-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)pyridin-3-ylamino)acetate (20 mg, 0.04 mmol) was added to a solution of ammonia (5 mL 7N in methanol) and H2O (5 mL). The mixture was stirred at 60° C. for 4 h. After evaporated to dryness, the residue was purified by silica gel chromatography, eluting with PE/EtOAc (1:1, v/v) to afford pure product as a brown powder (9.2 mg, 26%). 1H-NMR (CDCl3): δ 3.80 (d, 2H, J=1.6 Hz, CH2), 3.87 (s, 6H, 2×OCH3), 3.87 (s, 3H, OCH3), 4.01 (s, 3H, OCH3), 4.16 (s, 2H, CH2), 5.43 (s, 1H, NH), 6.12 (s, 2H, Ph-H), 6.75 (d, 1H, J=2.0 Hz, Py-H), 7.09 (d, 1H, J=15.6 Hz, CH), 7.56 (d, 1H, J=2.0 Hz, Py-H), 7.81 (d, 1H, J=15.6 Hz, CH); HR-MS (ESI+) m/z 452.1560 [M+H]+ C20H25N3O7S requires 451.1413.

Workup

  1. customAfter evaporated to dryness
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with PE/EtOAc (1:1

Sources & evidence

ORD record
ord-333d411dc3d745558d13f7b12f1cbf33
Source dataset
uspto-grants-2014_09
Patent number
US08829003B2

Reaction notes

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