HCID 71255517, compound → Ziresovir

HRID 540214Notes

Reaction equation

HRID 540214 reaction equation
C([N:8](CC1C=CC=CC=1)[C:9]1([CH2:13][NH:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([CH3:25])[CH:23]=3)[N:18]=[C:17]([N:26]3[CH2:32][C:31]4[CH:33]=[CH:34][CH:35]=[CH:36][C:30]=4[S:29](=[O:38])(=[O:37])[CH2:28][CH2:27]3)[N:16]=2)[CH2:12][O:11][CH2:10]1)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[NH2:8][C:9]1([CH2:13][NH:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([CH3:25])[CH:23]=3)[N:18]=[C:17]([N:26]3[CH2:32][C:31]4[CH:33]=[CH:34][CH:35]=[CH:36][C:30]=4[S:29](=[O:38])(=[O:37])[CH2:28][CH2:27]3)[N:16]=2)[CH2:10][O:11][CH2:12]1

Participants

4

Reactant 1

HCID 71255517HCID 71255517, compound

Product 1

HCID 71262247ZiresovirYield 30.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-{[3-(dib enzylamino)oxetan-3-yl]methyl}-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinazolin-4-amine (1.4 g, 2.26 mmol) in methanol was added palladium hydroxide (20% on carbon, 200 mg). After being stirred at room temperature overnight under a hydrogen atmosphere, the resulting mixture was filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel to afford 300 mg of the product as off-white foam. MS obsd. (ESI+) [(M+H)+] 440, 1H NMR (400 MHz, CD3OD) δ ppm 7.97 (d, J=7.6 Hz, 1 H), 7.86 (d, J=7.2 Hz, 1 H), 7.69 (s, 1 H), 7.58 (t, J=7.2 Hz, 1 H), 7.44-7.34 (m, 3 H), 5.21 (s, 2 H), 4.66 (d, J=6.4 Hz, 2 H), 4.60 (br.s., 2 H), 4.56 (d, J=6.4 Hz, 2 H), 4.10 (s, 2 H), 3.52 (t, J=5.2 Hz, 2 H), 2.39 (s, 3 H).

Workup

  1. filtrationthe resulting mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c38ad6236e104d359b61667081e95c66
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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