Dichloromethane → (E)-3-(5-methyl-4-oxo-1,2,3,4,5,6-hexahydropyrido[2,3-b][1,5]diazocin-8-yl)acrylic acid hydrochloride

HRID 1880011Notes

Reaction equation

HRID 1880011 reaction equation
[CH3:1][N:2]1[C:9](=[O:10])[CH2:8][CH2:7][NH:6][C:5]2[N:11]=[CH:12][C:13](/[CH:15]=[CH:16]/[C:17]([O:19]C(C)(C)C)=[O:18])=[CH:14][C:4]=2[CH2:3]1.C(O)(C(F)(F)F)=O.C(Cl)[Cl:32]>>[ClH:32].[CH3:1][N:2]1[C:9](=[O:10])[CH2:8][CH2:7][NH:6][C:5]2[N:11]=[CH:12][C:13](/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])=[CH:14][C:4]=2[CH2:3]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 59332864(E)-tert-butyl 3-(5-methyl-4-oxo-1,2,3,4,5,6-hexahydropyrido[2,3-b][1,5]diazocin-8-yl)acrylate

Product 1

HCID 68413470(E)-3-(5-methyl-4-oxo-1,2,3,4,5,6-hexahydropyrido[2,3-b][1,5]diazocin-8-yl)acrylic acid hydrochloride

Procedure

A suspension of (E)-tert-butyl 3-(5-methyl-4-oxo-1,2,3,4,5,6-hexahydropyrido[2,3-b][1,5]diazocin-8-yl)acrylate (391 mg, 1.23 mmol) in CH2Cl2 (10 mL) was treated with TFA (10 mL). After stirring at room temperature for 2 h, the solution was concentrated in vacuo. The resulting oil was treated with anhydrous HCl in dioxane (4 mL, 4.0 M) and sonicated until the oil was converted to a fine off-white solid. After stirring for 20 min, the suspension was concentrated. The solid was washed with Et2O, isolated by filtration and dried under vacuum. Yield: 388 mg (quant); 1H NMR (400 MHz, CDCl3) δ 8.17 (s, 1H), 8.04 (s, 1H), 7.48 (d, J=16.0 Hz, 1H), 6.48 (d, J=16.0 Hz, 1H), 4.78 (bs, 1H), 3.90 (s, 2H), 2.99 (s, 2H), 2.79 (s, 2H), 2.58 (s, 3H); ESI MS m/z 298 [C13H15N3O3+H]+

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. additionThe resulting oil was treated with anhydrous HCl in dioxane (4 mL, 4.0 M)
  3. customsonicated until the oil
  4. stirringAfter stirring for 20 min
  5. concentrationthe suspension was concentrated
  6. washThe solid was washed with Et2O
  7. customisolated by filtration
  8. customdried under vacuum

Sources & evidence

ORD record
ord-3e6e17abe52241808b1add10d8e48a23
Source dataset
uspto-grants-2012_11
Patent number
US08318720B2

Reaction notes

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