Hydrochloric Acid → HCID 178522946, compound

HRID 1070604

Reaction equation

HRID 1070604 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:31])[N:12]=[C:13]3[CH:20]=[CH:19][C:18]([C:21]#[C:22][CH2:23][O:24]C4CCCCO4)=[CH:17][N:14]3[C:15]=2[OH:16])=[O:9])=[CH:4][CH:3]=1.Cl>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:31])[N:12]=[C:13]3[CH:20]=[CH:19][C:18]([C:21]#[C:22][CH2:23][OH:24])=[CH:17][N:14]3[C:15]=2[OH:16])=[O:9])=[CH:32][CH:33]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178522945HCID 178522945, compound

Product 1

HCID 178522946HCID 178522946, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

N-(4-Chlorobenzyl)-4-hydroxy-2-oxo-7-(3-(tetrahydro-2H-pyran-2-yloxy)-1-propynyl)-2H-pyrido[1,2-a]pyrimidine-3-carboxamide (Preparation 7, 12 mg) is dissolved in CH2Cl2 and treated with 0.5 M HCl in methanol (0.5 mL). The reaction mixture is stirred for 16 h at room temperature. The mixture is concentrated, and the residue is crystallized from ether/hexanes and dried to afford 7 mg of the title compound as a brown solid. Physical characteristics: 1H NMR (CD3OD) δ9.2, 8.35, 7.75, 7.4-7.5, 4.80, 4.50; MS (ESI+) m/z 386 (M+H)+.

Workup

  1. concentrationThe mixture is concentrated
  2. customthe residue is crystallized from ether/hexanes
  3. customdried

Sources & evidence

ORD record
ord-e2ddaf5c2a2842ea8b4cb3639a77cc68
Source dataset
uspto-grants-2005_06
Patent number
US06903097B2

Linked notes

Loading…