Butylamine → (E)-3-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-N-butyl-acrylamide

HRID 660601Notes

Reaction equation

HRID 660601 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11](/[CH:23]=[CH:24]/[C:25](O)=[O:26])[CH:12]=[CH:13][C:14]=1[N:15]1[CH2:19][C:18](=[O:20])[NH:17][S:16]1(=[O:22])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1[CH:29]=[CH:30][C:31]2N(O)N=[N:34][C:32]=2C=1.CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C.C(N)CCC>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11](/[CH:23]=[CH:24]/[C:25]([NH:34][CH2:32][CH2:31][CH2:30][CH3:29])=[O:26])[CH:12]=[CH:13][C:14]=1[N:15]1[CH2:19][C:18](=[O:20])[NH:17][S:16]1(=[O:21])=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 8007ButylamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68839439HCID 68839439, compound

Product 1

HCID 68837808(E)-3-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-N-butyl-acrylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (E)-3-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acrylic acid (10 mg, 0.25 mmol) in THF (4 mL) is added HOBt (68 mg, 0.5 mmol). After 10 min EDCl (96 mg, 0.5 mmol) and triethylamine (0.104 mL, 0.75 mmol) are added and the solution is stirred for 30 min then a solution of n-butylamine in 2 mL THF is added and the mixture is stirred at RT for 6 h. The solvent is removed under reduced pressure to afford the title compound: (M−1)−=442.

Workup

  1. stirringthe mixture is stirred at RT for 6 h
  2. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-5e62d7315351478a864451f927e52d33
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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