HCID 90419042, compound → HCID 90419005, compound

HRID 2202392Notes

Reaction equation

HRID 2202392 reaction equation
[F:1][C:2]1[C:7]2=[N:8]S[N:10]=[C:6]2[C:5]([S:11]([NH:14][C:15]2[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1>CC(O)=O.O.[Zn]>[NH2:10][C:6]1[C:7]([NH2:8])=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[S:11]([NH:14][C:15]1[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=1)(=[O:12])=[O:13]

Participants

4

Reactant 1

HCID 90419042HCID 90419042, compound

Product 1

HCID 90419005HCID 90419005, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 21899381Acetic acid--water (1/1)Solvent

Conditions

Temperature
70 °C

Procedure

To a solution of the compound 39D (382 mg, 1.0 mmol) in AcOH/H2O (8 mL/3 mL) at 70° C. was added zinc powder (975 mg, 15 mmol) and the resulting suspension was stirred at 70° C. for 1 h. The solid was filtered off and washed with EtOAc. The filtrate was partitioned between satd. NaHCO3 and EtOAc. The organic layer was separated and washed with water and brine, dried over anhydrous Na2SO4 and concentrated to give crude product 39E, which was confirmed by LCMS, and used in the next reaction without further purification. LC-MS: m/z 354.4 (M+H)+.

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with EtOAc
  3. customThe filtrate was partitioned between satd
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f5eb6c5a6f2d40a4992d6172f418c668
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

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