HCID 58055052, compound → HCID 58055076, compound

HRID 1685051Notes

Reaction equation

HRID 1685051 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][NH:6][C:7](=[O:20])[NH:8][C:9]1[S:10][C:11]([F:19])=[C:12]([CH2:14][N:15](OC)[CH3:16])[N:13]=1>C(O)(=O)C.O.[Zn]>[F:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][NH:6][C:7](=[O:20])[NH:8][C:9]1[S:10][C:11]([F:19])=[C:12]([CH2:14][NH:15][CH3:16])[N:13]=1

Participants

5

Reactant 1

HCID 58055052HCID 58055052, compound

Product 1

HCID 58055076HCID 58055076, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 2-(3-(3-fluorobenzyl)ureido)-4-(N-methoxy-N-methyl-aminomethyl)-5-fluorothiazole (2.05 g, 6 mmol) in glacial acetic acid (30 mL) was treated with micronized zinc dust (12 g) and stirred at 60 C for 1-2 hours. The mixture was diluted with water (30 mL) and filtered on Celite. The filter cake was washed with 1:1 HOAc:water (3×20 mL) and the combined filtrate were brought to pH 10 with ammonium hydroxide (−82 mL). The resulting mixture was stirred in ice and the crude product was collected by filtration and washed with water (4 mL). The crude product was further purified by silica gel chromatography (5:94:1 MeOH:DCM:NH4OH) to afford Intermediate 40 as a white solid (1.25 g, 67% yield).

Workup

  1. filtrationfiltered on Celite
  2. washThe filter cake was washed with 1:1 HOAc
  3. stirringThe resulting mixture was stirred in ice
  4. filtrationthe crude product was collected by filtration
  5. washwashed with water (4 mL)
  6. customThe crude product was further purified by silica gel chromatography (5:94:1 MeOH:DCM:NH4OH)

Sources & evidence

ORD record
ord-c25f20107e7746a889d09dcb83099b48
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

Loading…