Sodium Bicarbonate → N-[4-(2-Furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]tetrahydrofuran-3-carboxamide

HRID 337507Notes

Reaction equation

HRID 337507 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([C:6]([OH:8])=O)[CH2:2]1.CCN=C=NCCCN(C)C.Cl.O.ON1C2C=CC=CC=2N=N1.[O:32]1[CH2:37][CH2:36][CH:35]([C:38]([C:40]2[S:44][C:43]([NH2:45])=[N:42][C:41]=2[C:46]2[O:47][CH:48]=[CH:49][CH:50]=2)=[O:39])[CH2:34][CH2:33]1.C(=O)([O-])O.[Na+]>>[O:47]1[CH:48]=[CH:49][CH:50]=[C:46]1[C:41]1[N:42]=[C:43]([NH:45][C:6]([CH:3]2[CH2:4][CH2:5][O:1][CH2:2]2)=[O:8])[S:44][C:40]=1[C:38]([CH:35]1[CH2:36][CH2:37][O:32][CH2:33][CH2:34]1)=[O:39]

Participants

6

Reactant 5

HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 4661317(R)-Tetrahydro-3-furoic acidHCID 866124682-Amino-4-(2-furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazole

Product 1

HCID 23144235N-[4-(2-Furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]tetrahydrofuran-3-carboxamideYield 84%

Conditions

Temperature
60 °C

Procedure

Tetrahydrofuran-3-carboxylic acid (1.72 mL, 1.8 mmol), EDC hydrochloride (344 mg, 1.80 mmol) and 1-hydroxybenzotriazole monohydrate (276 mg, 1.80 mmol) were added to Compound 454 (125 mg, 0.450 mmol), followed by stirring at 60° C. for 3.5 hours. The reaction mixture was poured into a saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was reslurried with diethyl ether to afford the entitled Compound 524 (142 mg, 84%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-f15067f383364eea837628d129b5fdfb
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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