Hydrochloric Acid → HCID 58456088, compound

HRID 410688Notes

Reaction equation

HRID 410688 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[S:23][C:22]([CH2:24][CH2:25][C:26]3[CH:35]=[CH:34][C:29]([C:30]([O:32]C)=[O:31])=[CH:28][CH:27]=3)=[N:21][CH:20]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1.[OH-].[Na+].Cl>CO.O>[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[S:23][C:22]([CH2:24][CH2:25][C:26]3[CH:27]=[CH:28][C:29]([C:30]([OH:32])=[O:31])=[CH:34][CH:35]=3)=[N:21][CH:20]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67432945HCID 67432945, compound

Product 1

HCID 58456088HCID 58456088, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

The product of Step 1 (65 mg, 0.130 mmol) was taken up in MeOH (2.0 ml) in a microwave vial, and 1.0M sodium hydroxide (0.261 ml, 0.261 mmol) was added. The reaction was heated to 100° C. for 10 min in the microwave. The colorless solution was adjusted to a pH of 3-4 with 1 N HCl, diluted with water, and extracted with 15% IPA/CHCl3 (2×). The combined organic layers were dried (MgSO4) and evaporated to afford the title compound (60 mg, 0.124 mmol, 95% yield) as a colorless solid. MS ESI: [M+H]+ m/z 485.0 1H NMR (500 MHz, DMSO-d6) δ 12.82 (s, 1H), 10.24 (s, 1H), 8.81 (d, J=4.9, 1H), 7.94 (s, 1H), 7.92 (s, 1H), 7.84 (d, J=8.1, 2H), 7.43 (s, 1H), 7.39 (d, J=8.1, 2H), 7.27 (d, J=4.9, 1H), 7.12 (s, 1H), 3.41-3.20 (m, 2H), 3.13 (t, J=7.6, 2H), 2.29 (s, 3H). rhSYK activity=+++

Workup

  1. additionwas added
  2. extractionextracted with 15% IPA/CHCl3 (2×)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-efced3acbfd949c88e789f3bf62a0925
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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