Triethylamine → HCID 90021697, compound

HRID 1754843Notes

Reaction equation

HRID 1754843 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]([OH:11])=[CH:4][CH:3]=1.O.ON1C2C=CC=CC=2N=N1.Cl.[CH:24]([C:27]1[S:28][CH:29]=[C:30]([CH2:32][CH2:33][NH2:34])[N:31]=1)([CH3:26])[CH3:25].CCN(CC)CC.Cl.CN(C)CCCN=C=NCC>C1COCC1.O.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([NH:34][CH2:33][CH2:32][C:30]1[N:31]=[C:27]([CH:24]([CH3:26])[CH3:25])[S:28][CH:29]=1)=[O:9]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 94475-Chlorosalicylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 50944174HCID 50944174, compound

Product 1

HCID 90021697HCID 90021697, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 5-chlorosalicylic acid (863 mg, 5.0 mmol, 1.0 eq.) in THF (3 mL) and water (4 mL), 1-hydroxybenzotriazole hydrate (1.01 g, 7.5 mmol, 1.5 eq.) was added. The resulting solution was stirred at r.t. for 30 minutes. Then 2-(2-isopropyl-1,3-thiazol-4-yl)ethanamine hydrochloride (1.03 g, 5.0 mmol, 1.0 eq.) in THF (3 mL) and NEt3 (1.39 mL, 10.0 mmol, 2.0 eq) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.44 g, 7.5 mmol, 1.5 eq) in water (4 mL) were added in sequence. The resulting mixture was stirred at r.t. for 18 hours. The reaction mixture was poured in sat. aq. NaHCO3 (75 mL). The mixture was extracted with AcOEt (2×50 mL). The comb. org. phases were washed with 1M aq. HCl soln. (50 mL) and sat. aq. NaCl soln. (1×20 mL), dried over MgSO4, and concentrated in vacuo to give the desired amide as a brown oil. The product was used without further purification.

Workup

  1. stirringThe resulting mixture was stirred at r.t. for 18 hours
  2. extractionThe mixture was extracted with AcOEt (2×50 mL)
  3. washphases were washed with 1M aq. HCl soln
  4. dry with material(1×20 mL), dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c2483c117934fb1bd49ee0d8b9fafad
Source dataset
uspto-grants-2015_10
Patent number
US09169270B2

Reaction notes

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