1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-(Benzo[2,1,3]thiadiazol-5-yloxy)-N-[4-(1-hydroxy-1-methyl-ethyl)-benzyl]-nicotinamide

HRID 899391Notes

Reaction equation

HRID 899391 reaction equation
[N:1]1[S:2][N:3]=[C:4]2[CH:9]=[C:8]([O:10][C:11]3[N:19]=[CH:18][CH:17]=[CH:16][C:12]=3[C:13]([OH:15])=O)[CH:7]=[CH:6][C:5]=12.[NH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([OH:31])([CH3:30])[CH3:29])=[CH:24][CH:23]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.O>[N:1]1[S:2][N:3]=[C:4]2[CH:9]=[C:8]([O:10][C:11]3[N:19]=[CH:18][CH:17]=[CH:16][C:12]=3[C:13]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([OH:31])([CH3:29])[CH3:30])=[CH:24][CH:23]=3)=[O:15])[CH:7]=[CH:6][C:5]=12

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 101542112-[4-(aminomethyl)phenyl]propan-2-olHCID 226101592-(Benzo[2,1,3]thiadiazol-5-yloxy)-nicotinic acid

Product 1

HCID 101128632-(Benzo[2,1,3]thiadiazol-5-yloxy)-N-[4-(1-hydroxy-1-methyl-ethyl)-benzyl]-nicotinamideYield 63.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-(Benzo[2,1,3]thiadiazol-5-yloxy)-nicotinic acid (30.8 mg, 0.11 mmol), 2-(4-aminomethyl-phenyl)-propan-2-ol (18.6 mg, 0.11 mmol), 1-hydroxybenzotriazole hydrate (16.8 mg, 0.12 mmol), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (25.9 mg, 0.14 mmol) were dissolved in N,N-dimethylformamide (10 ml) and stirred at room temperature over night. The solution was poured into water (30 ml) and extracted with ethyl acetate. The combined organic layers were washed successively with 1N NaOH, water, and brine, then dried over sodium sulfate and concentrated in vacuo. The resulting amber oil was purified by flash column chromatography (1:1 ethyl acetate/hexane) to afford a white foam (29 mg, 0.07 mmol).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed successively with 1N NaOH, water, and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting amber oil was purified by flash column chromatography (1:1 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-446eb578c7634997adb17f54e0065a8a
Source dataset
uspto-grants-2008_04
Patent number
US07354941B2

Reaction notes

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