Dichloromethane → HCID 66966635, compound

HRID 2097205Notes

Reaction equation

HRID 2097205 reaction equation
[O:1]=[C:2]1[NH:11][C:10]2[N:9]=[CH:8][C:7](/[CH:12]=[CH:13]/[C:14]([O:16]C(C)(C)C)=[O:15])=[CH:6][C:5]=2[CH:4]=[CH:3]1.FC(F)(F)C(O)=O.C(Cl)[Cl:29]>>[ClH:29].[O:1]=[C:2]1[NH:11][C:10]2[N:9]=[CH:8][C:7](/[CH:12]=[CH:13]/[C:14]([OH:16])=[O:15])=[CH:6][C:5]=2[CH:4]=[CH:3]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 59277577HCID 59277577, compound

Product 1

HCID 66966635HCID 66966635, compound

Procedure

A suspension of (E)-tert-butyl 3-(7-oxo-7,8-dihydro-1,8-naphthyridin-3-yl)acrylate (500 mg, 1.84 mmol) in CH2Cl2 (7 mL) was treated with trifluoroacetic acid (7 mL). The mixture became homogeneous and it was stirred at room temperature for 1 h. The solution was concentrated to dryness and treated with 4M HCl in dioxane (5 mL). The suspension was sonicated for 20 min, diluted with Et2O (50 mL) and sonicated for an additional 20 min. The solid was filtered and dried under reduced pressure overnight. Yield: 450 mg (96.8%) 1H-NMR (300 MHz, DMSO-d6) δ 12.4 (br s, 1H), 8.82 (s, 1H), 8.52 (s, 1H), 7.91 (d, 1H, J=9.0 Hz), 7.67 (d, 1H, J=15.0 Hz), 6.67 (d, 1H, J=15.0 Hz), 6.61 (m, 1H); ESI MS m/z 217 [C11H8N2O3+]+

Workup

  1. concentrationThe solution was concentrated to dryness
  2. additiontreated with 4M HCl in dioxane (5 mL)
  3. customThe suspension was sonicated for 20 min
  4. additiondiluted with Et2O (50 mL)
  5. customsonicated for an additional 20 min
  6. filtrationThe solid was filtered
  7. customdried under reduced pressure overnight

Sources & evidence

ORD record
ord-c665e37a57854110a8ee28c55e03f49a
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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