Peracetic Acid → HCID 66917033, compound

HRID 2390509Notes

Reaction equation

HRID 2390509 reaction equation
[C:1]([C:5]1[CH:31]=[CH:30][CH:29]=[CH:28][C:6]=1[O:7][C:8]1[C:13]([NH:14][C:15]2[S:19][N:18]=[C:17]([CH2:20][S:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:16]=2)=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].C(OO)(=[O:34])C>C(Cl)Cl.C(OCC)(=O)C>[C:1]([C:5]1[CH:31]=[CH:30][CH:29]=[CH:28][C:6]=1[O:7][C:8]1[C:13]([NH:14][C:15]2[S:19][N:18]=[C:17]([CH2:20][S:21]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:34])[N:16]=2)=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 6585Peracetic AcidHCID 59128968HCID 59128968, compound

Product 1

HCID 66917033HCID 66917033, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(2-tert-butylphenoxy)-N-(3-(phenylthiomethyl)-1,2,4-thiadiazol-5-yl)pyridin-3-amine (Example 470) (250 mg, 0.56 mmol), peracetic acid (32% wt/v, 132 μL, 0.56 mmol in DCM (3 mL) was stirred at rt for 2 h. The reaction mixture was diluted in ethyl acetate and washed with saturated sodium bicarbonate. The organic phase was separated, dried (MgSO4), filtered and evaporated. The crude product was purified by preparative HPLC to give Example 471. (M+H)+=465; 1H NMR (400 MHz, DMSO d6) δ ppm 1.29 (s, 9 H), 4.33 (d, J=13.13 Hz, 1 H), 4.42 (d, J=13.13 Hz, 1 H), 6.91 (td, J=7.84, 1.51 Hz, 1 H), 7.08 (dd, J=7.84, 4.80, 1H), 7.16 (dt, J=7.58, 1.52, 1H), 7.22 (td, J=7.32, 1.76, 1H), 7.41 (dd, J=7.83, 1.52 Hz, 1 H), 7.5-7.7 (m, 5H), 7.75 (dd, J=4.80, 1.51 Hz, 1 H), 8.45 (dd, J=7.83, 1.51 Hz, 1H), 10.84 (s, 1 H).

Workup

  1. washwashed with saturated sodium bicarbonate
  2. customThe organic phase was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by preparative HPLC
  7. customto give Example 471

Sources & evidence

ORD record
ord-cbe3b3ac3be14aad9cd6f278af910324
Source dataset
uspto-grants-2012_09
Patent number
US08273772B2

Reaction notes

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