Triethylsilane → HCID 178461231, compound

HRID 1852882Notes

Reaction equation

HRID 1852882 reaction equation
C([O:8][C:9]1[C:14]([C:15]2[C:20]3[N:21]([CH2:33][C@H:34]4[CH2:39][CH2:38][C@H:37]([CH3:40])[CH2:36][CH2:35]4)[C:22]([N:24]4[CH2:29][CH2:28][O:27][C@@H:26]5[CH2:30][CH2:31][CH2:32][C@@H:25]45)=[N:23][C:19]=3[CH:18]=[C:17]([C:41]3[NH:45][C:44](=[O:46])[O:43][N:42]=3)[N:16]=2)=[CH:13][C:12]([Cl:47])=[CH:11][N:10]=1)C1C=CC=CC=1.[SiH](CC)(CC)CC>C(Cl)Cl.Cl[Pd]Cl>[Cl:47][C:12]1[CH:13]=[C:14]([C:15]2[C:20]3[N:21]([CH2:33][C@H:34]4[CH2:35][CH2:36][C@H:37]([CH3:40])[CH2:38][CH2:39]4)[C:22]([N:24]4[CH2:29][CH2:28][O:27][C@@H:26]5[CH2:30][CH2:31][CH2:32][C@@H:25]45)=[N:23][C:19]=3[CH:18]=[C:17]([C:41]3[NH:45][C:44](=[O:46])[O:43][N:42]=3)[N:16]=2)[C:9](=[O:8])[NH:10][CH:11]=1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 178461229HCID 178461229, compound

Product 1

HCID 178461231HCID 178461231, compound

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-{4-[2-(benzyloxy)-5-chloropyridin-3-yl]-2-[(4aR,7aR)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridin-6-yl}-1,2,4-oxadiazol-5(4H)-one (23 mg, 0.03 mmol) in anhydrous CH2Cl2 at 0° C., Et3SiH (0.029 mL, 0.18 mmol) and PdCl2 (2 mg, 0.01 mmol) were added. The reaction was stirred at 0° C. for 0.5 hour and then concentrated. The residue was purified on a C-18 column eluting with 40% water/60% acetonitrile to afford 5-chloro-3-{2-[(4aR,7aR)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-3-[(trans-4-methylcyclohexyl)methyl]-6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-3H-imidazo[4,5-c]pyridin-4-yl}pyridin-2(1H)-one. 1H NMR (400 MHz, CD3OD) δ 8.09 (s, 1H), 8.04 (br s, 1H), 7.76 (d, J=2.8 Hz, 1H), 4.01 (m, 1H), 3.83-3.93 (m, 3H), 3.62 (m, 1H), 3.54 (m, 1H), 3.38 (m, 1H), 3.12 (m, 1H), 2.96 (m, 1H), 2.28 (m, 1H), 1.97 (m, 1H), 1.49-1.82 (m, 6H), 1.19-1.25 (m, 2H), 0.91-1.00 (m, 2H), 0.78 (d, J=6.4 Hz, 3H), 0.57-0.74 (m, 3H). MS ES calc'd. for C28H32ClN7O4 [M+H]+ 566. found 566.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified on a C-18 column
  3. washeluting with 40% water/60% acetonitrile

Sources & evidence

ORD record
ord-910779c8cdca442fbe1c428a98e8399b
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Reaction notes

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