Hydrochloric Acid → HCID 86661295, compound

HRID 1685033Notes

Reaction equation

HRID 1685033 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:9]=[C:10]([CH:29]=[CH:30][CH:31]=1)[CH2:11][NH:12][C:13](=[O:28])[NH:14][C:15]1[S:16][CH:17]=[C:18]([C:20](=[N:26]O)[C:21](OCC)=[O:22])[N:19]=1.OS([O-])(=O)=O.[Na+].Cl>CO.C1COCC1>[NH2:26][CH:20]([C:18]1[N:19]=[C:15]([NH:14][C:13]([NH:12][CH2:11][C:10]2[CH:29]=[CH:30][CH:31]=[C:8]([F:7])[CH:9]=2)=[O:28])[S:16][CH:17]=1)[CH2:21][OH:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516919Sodium BisulfateHCID 21226445Aluminium lithium hydrideHCID 86661296HCID 86661296, compound

Product 1

HCID 86661295HCID 86661295, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (10 mL, 10 mmol, 1 M in THF) was added to a THF (20 mL) solution of ethyl 2-(2-(3-(3-fluorobenzyl)ureido)thiazol-4-yl)-2-(hydroxyimino)acetate (1.05 g, 2.86 mmol). The mixture was stirred for a day at 50 C. Upon cooling the mixture to 0 C, Na2SO4x10H2O (9.2 g, 28.6 mmol) was added carefully. The suspension was stirred for two days at ambient temperature which was followed by the addition of NaHSO4 (1.2 g, 28.6 mmol) and MeOH (20 mL). The mixture is further stirred for an hour then HCl (5 mL, 2 M in ether) was added. Stirring was continued for another hour. Filtration, evaporation of the filtrate and Flash chromatography afforded 1-(4-(1-amino-2-hydroxyethyl)thiazol-2-yl)-3-(3-fluorobenzyl)urea. 1H NMR (400 MHz, MeOH): δ 7.28 (m, 1H), 7.09 (d, 1H), 7.01 (d, 1H), 6.92 (td, 1H), 6.81 (s, 1H), 4.42 (s, 2H), 4.10 (m, 1H), 3.84 (dd, 1H), 3.72 (dd, 1H). MS (ES+): M/Z 311 (M+H)+.

Workup

  1. temperatureUpon cooling the mixture to 0 C, Na2SO4x10H2O (9.2 g, 28.6 mmol)
  2. additionwas added carefully
  3. stirringThe suspension was stirred for two days at ambient temperature which
  4. stirringThe mixture is further stirred for an hour
  5. stirringStirring
  6. waitwas continued for another hour
  7. filtrationFiltration, evaporation of the filtrate and Flash chromatography

Sources & evidence

ORD record
ord-9ad12febca5745468392925102506eaf
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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