HCID 59620087, compound → HCID 59619872, compound

HRID 445726Notes

Reaction equation

HRID 445726 reaction equation
[CH:1]([N:4]1[CH:8]=[C:7]([N:9]2[C:21]3[C:20]4[CH:19]=[C:18]([C:22]5[CH:33]=[N:32][C:25]6[N:26](C)[C:27](=O)[O:28][CH2:29][C:24]=6[CH:23]=5)[CH:17]=[CH:16][C:15]=4[N:14]=[CH:13][C:12]=3[N:11]([CH3:34])[C:10]2=[O:35])[C:6]([CH3:36])=[N:5]1)([CH3:3])[CH3:2]>O1CCOCC1.[Li+].[OH-].CCOC(C)=O>[OH:28][CH2:29][C:24]1[CH:23]=[C:22]([C:18]2[CH:17]=[CH:16][C:15]3[N:14]=[CH:13][C:12]4[N:11]([CH3:34])[C:10](=[O:35])[N:9]([C:7]5[C:6]([CH3:36])=[N:5][N:4]([CH:1]([CH3:3])[CH3:2])[CH:8]=5)[C:21]=4[C:20]=3[CH:19]=2)[CH:33]=[N:32][C:25]=1[NH:26][CH3:27]

Participants

5

Reactant 1

HCID 59620087HCID 59620087, compound

Product 1

HCID 59619872HCID 59619872, compound

Reagents, catalysts & solvents 3

HCID 3939Lithium HydroxideSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-(1-isopropyl-3-methyl-1H-pyrazol-4-yl)-3-methyl-8-(1-methyl-2-oxo-1,4-dihydro-2H-pyrido[2,3-d][1,3]oxazin-6-yl)-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Example 170, 0.04 mmol) in dioxane (0.32 ml) and 1 M aqueous LiOH (0.08 ml) was stirred for 1.5 h at rt. The reaction mixture was diluted with EtOAc and quenched with 2 M aqueous HCl (0.12 ml) and water. Then was added saturated aqueous NaHCO3 and the aqueous layer was extracted with EtOAc (2×). The combined organic layers were dried over Na2SO4, filtered, evaporated and dried under vacuum to give the title compound as an off-white solid. (HPLC: tR 2.09 min (Method A); M+H=458 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.90 (s, 1H), 8.20 (s, 1H), 8.09-8.01 (m, 2H), 7.83-7.79 (m, 1H), 7.52-7.49 (m, 1H), 7.45-7.42 (m, 1H), 6.10 (q, br, 1H), 5.21 (t, 1H), 4.56 (qt, 1H), 4.38 (d, 2H), 3.57 (s, 3H), 2.86 (d, 3H), 1.95 (s, 3H), 1.49-1.45 (m, 6H))

Workup

  1. customquenched with 2 M aqueous HCl (0.12 ml) and water
  2. additionThen was added saturated aqueous NaHCO3
  3. extractionthe aqueous layer was extracted with EtOAc (2×)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customdried under vacuum

Sources & evidence

ORD record
ord-63571402c0af437dafead793ee147007
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

Loading…