Methanol → HCID 58456112, compound

HRID 410679Notes

Reaction equation

HRID 410679 reaction equation
[OH-].[K+].CO.[CH3:5][O:6][C@:7]1([C:19]2[S:20][C:21]([C:24]3[CH:29]=[C:28]([NH:30][C:31]4[N:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[CH:33][N:32]=4)[CH:27]=[C:26]([CH3:41])[CH:25]=3)=[CH:22][N:23]=2)[CH2:12][CH2:11][C@H:10]([C:13]([O:15]C)=[O:14])[C:9]([CH3:18])([CH3:17])[CH2:8]1>>[CH3:5][O:6][C@:7]1([C:19]2[S:20][C:21]([C:24]3[CH:29]=[C:28]([NH:30][C:31]4[N:36]=[C:35]([C:37]([F:38])([F:39])[F:40])[CH:34]=[CH:33][N:32]=4)[CH:27]=[C:26]([CH3:41])[CH:25]=3)=[CH:22][N:23]=2)[CH2:12][CH2:11][C@H:10]([C:13]([OH:15])=[O:14])[C:9]([CH3:18])([CH3:17])[CH2:8]1

Participants

4

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 67433792HCID 67433792, compound

Product 1

HCID 58456112HCID 58456112, compoundYield 79.3%

Conditions

Temperature
65 °C

Procedure

Potassium hydroxide in methanol (3.0 mL, 3.0 mmol) was added to the product of Step 2 (150 mg, 0.23 mmol) and the reaction mixture heated to 65° C. for 110 h. The reaction mixture was cooled and then quenched with HCl (2N in H2O). The mixture was filtered and washed with ˜20 mL of water to obtain an off-white solid. The solid was dried under reduced pressure at 40° C. in a vacuum oven for 1.5 h to provide the title compound (95 mg, 79%) as a yellow solid. ESI: [M+H]+ m/z 521. 1H NMR (500 MHz, DMSO-d6) δ 12.15-11.94 (m, 1H), 10.26 (s, 1H), 8.83 (d, J=4.9, 1H), 8.00 (s, 1H), 7.96 (s, 1H), 7.45 (s, 1H), 7.28 (d, J=4.9, 1H), 7.16 (s, 1H), 3.07 (s, 3H), 2.31 (s, 3H), 2.22-2.09 (m, 2H), 1.99-1.80 (m, 3H), 1.72 (d, J=14.5, 1H), 1.62 (s, 11.1), 1.07 (s, 3H), 1.01 (s, 3H). rhSYK activity=+++

Workup

  1. temperatureThe reaction mixture was cooled
  2. customquenched with HCl (2N in H2O)
  3. filtrationThe mixture was filtered
  4. washwashed with ˜20 mL of water
  5. customto obtain an off-white solid
  6. customThe solid was dried under reduced pressure at 40° C. in a vacuum oven for 1.5 h

Sources & evidence

ORD record
ord-91eb73797c9a45268227f4ec0fb3ad5b
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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