Tetrahydrofuran → HCID 86661299, compound

HRID 1685035Notes

Reaction equation

HRID 1685035 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.[F:12][C:13]1[CH:14]=[C:15]([CH:33]=[CH:34][CH:35]=1)[CH2:16][NH:17][C:18](=[O:32])[NH:19][C:20]1[S:21][C:22]([CH:29]([CH3:31])[CH3:30])=[C:23]([C:25](OC)=[O:26])[N:24]=1.OS([O-])(=O)=O.[Na+]>CO>[F:12][C:13]1[CH:14]=[C:15]([CH:33]=[CH:34][CH:35]=1)[CH2:16][NH:17][C:18]([NH:19][C:20]1[S:21][C:22]([CH:29]([CH3:31])[CH3:30])=[C:23]([CH2:25][OH:26])[N:24]=1)=[O:32]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 516919Sodium BisulfateHCID 21226445Aluminium lithium hydrideHCID 86661297HCID 86661297, compound

Product 1

HCID 86661299HCID 86661299, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

LiAlH4 (5.5 mL, 5.5 mmol, 1 M in THF) was added to a THF (30 mL) solution of methyl 2-(3-(3-fluorobenzyl)ureido)-5-isopropylthiazole-4-carboxylate (780 mg, 2.22 mmol) at 0 C. Upon completion of the reaction Na2SO4x10H2O (1.5 g, 4.5 mmol) was added carefully. The suspension was stirred for a day at ambient temperature which was followed by the addition of NaHSO4 (0.5 g, 4.5 mmol) and MeOH (5 mL). The mixture extracted with CH2Cl2, washed with dilute HCl, dried and evaporated to afford 1-(3-fluorobenzyl)-3-(4-(hydroxymethyl)-5-isopropylthiazol-2-yl)urea. 1H NMR (400 MHz, CDCl3): δ 7.70 (s, 1H, br), 7.24 (m, 1H), 7.05 (d, 1H), 6.99 (d, 1H), 6.92 (td, 1H), 4.55 (s, 2H), 4.41 (d, 2H), 3.20 (m, 1H), 1.27 (d, 6H). MS (ES+): M/Z 324 (M+H)+.

Workup

  1. customUpon completion of the reaction Na2SO4x10H2O (1.5 g, 4.5 mmol)
  2. additionwas added carefully
  3. extractionThe mixture extracted with CH2Cl2
  4. washwashed with dilute HCl
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-23e8eb25db4b470784f8332d2ff4b9e6
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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