Peracetic Acid → 6,6-Dimethyl-2-[6-(6-methyl-1-oxidopyridin-3-yl)-2,3-dihydro-4h-1,4-benzoxazin-4-yl]-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-one

HRID 885972Notes

Reaction equation

HRID 885972 reaction equation
[CH3:1][C:2]1([CH3:29])[NH:7][C:6](=[O:8])[C:5]2[S:9][C:10]([N:12]3[C:17]4[CH:18]=[C:19]([C:22]5[CH:23]=[N:24][C:25]([CH3:28])=[CH:26][CH:27]=5)[CH:20]=[CH:21][C:16]=4[O:15][CH2:14][CH2:13]3)=[N:11][C:4]=2[CH2:3]1.C(OO)(=[O:32])C>C(Cl)Cl>[CH3:1][C:2]1([CH3:29])[NH:7][C:6](=[O:8])[C:5]2[S:9][C:10]([N:12]3[C:17]4[CH:18]=[C:19]([C:22]5[CH:23]=[N+:24]([O-:32])[C:25]([CH3:28])=[CH:26][CH:27]=5)[CH:20]=[CH:21][C:16]=4[O:15][CH2:14][CH2:13]3)=[N:11][C:4]=2[CH2:3]1

Participants

4

Reactant 2

HCID 6585Peracetic AcidHCID 445776396,6-dimethyl-2-(6-(6-methylpyridin-3-yl)-2,3-dihydrobenzo[b][1,4]oxazin-4-yl)-6,7-dihydrothiazolo[5,4-c]pyridin-4(5H)-one

Product 1

HCID 671863186,6-Dimethyl-2-[6-(6-methyl-1-oxidopyridin-3-yl)-2,3-dihydro-4h-1,4-benzoxazin-4-yl]-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-oneYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Example 48 (0.08 g, 0.19 mmol) in DCM (10 ml) was added peracetic acid (0.14 mL, 32 wt % in AcOH, 0.59 mmol). The reaction mixture was stirred at r.t. for 16 h, then concentrated in vacuo. Purification by preparative HPLC (Method 6) gave the title compound (0.014 g, 22%) as a white solid. δH (CD3OD) 8.53 (1H, d, J 1.5 Hz), 8.40 (1H, d, J 2.1 Hz), 7.69 (1H, dd, J 8.1 and 1.7 Hz), 7.55 (1H, d, J 8.3 Hz), 7.34 (1H, dd, J 8.7 and 2.3 Hz), 7.10 (1H, d, J 8.5 Hz), 4.46-4.37 (2H, m), 4.19-4.13 (2H, m), 2.92 (2H, s), 2.58 (3H, s), 1.41 (6H, s,). LCMS (ES+) 423.0 (M+H)+, RT 2.48 minutes (Method 1).

Workup

  1. concentrationconcentrated in vacuo
  2. customPurification by preparative HPLC (Method 6)

Sources & evidence

ORD record
ord-5627082f439c4431ae090d88967cc8a8
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

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