Hydrochloric Acid → HCID 178526950, compound

HRID 1004414Notes

Reaction equation

HRID 1004414 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:19][C:20]1[C:29]2[O:28][C:27]([C:30]3[NH:34][N:33]=[N:32][N:31]=3)=[CH:26][C:25](=[O:35])[C:24]=2[CH:23]=[CH:22][CH:21]=1.N12CCCN=C1CCCCC2.Cl.[C:48]([O-])(=[O:50])C.[Na+]>CN1CCCC1=O.O.CO.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[OH2:11].[O:35]=[C:25]1[C:24]2[CH:23]=[CH:22][CH:21]=[C:20]([NH:19][C:48](=[O:50])[C:15]3[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:13][CH:14]=3)[C:29]=2[O:28][C:27]([C:30]2[NH:34][N:33]=[N:32][N:31]=2)=[CH:26]1.[O:35]=[C:25]1[C:24]2[CH:23]=[CH:22][CH:21]=[C:20]([NH:19][C:48](=[O:50])[C:15]3[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:13][CH:14]=3)[C:29]=2[O:28][C:27]([C:30]2[NH:34][N:33]=[N:32][N:31]=2)=[CH:26]1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 517045Sodium AcetateHCID 108704574-(4-Phenylbutoxy)bromobenzeneHCID 178507421HCID 178507421, compound

Product 1

HCID 178526950HCID 178526950, compoundYield 78.7%

Reagents, catalysts & solvents 4

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 4-(4-phenylbutoxy)bromobenzene (0.50 g, 1.64 mmole), 8-amino-4-oxo-2-(tetrazol-5-yl)-4H-1-benzopyran (0.75 g, 3.28 mmole), bis-(triphenylphospine)palladium (II) chloride (0.135 g, 0.19 mmole) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.87 g, 5.74 mmole) was stirred in N-methylpyrrolidinone (10 ml) at 100-110° C. under an atmosphere of carbon monoxide at atmospheric pressure for 4.5 hours. The reaction mixture was diluted with water (15 ml) and acidified using concentrated hydrochloric acid (5 ml). The precipitate was filtered, washed with water and methanol and then stirred in concentrated hydrochloric acid (8 ml) to dissolve unreacted 8-amino-4-oxo-2-(tetrazol-5-yl)-4H-1-benzopyran. The undissolved solid was filtered, washed with concentrated hydrochloric (2×1.5 ml), water, then methanol. The damp cake was stirred with sodium acetate (0.15 g, 1.83 mmole) in methanol (10 ml) and the solution filtered. The supernatant liquor was acidified with concentrated hydrochloric acid (0.2 ml), and the product filtered, washed with methanol and dried to give the title compound (422 mg, 53%).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water and methanol
  3. dissolutionto dissolve unreacted 8-amino-4-oxo-2-(tetrazol-5-yl)-4H-1-benzopyran
  4. filtrationThe undissolved solid was filtered
  5. washwashed
  6. concentrationwith concentrated hydrochloric (2×1.5 ml), water
  7. filtrationthe solution filtered
  8. filtrationthe product filtered
  9. washwashed with methanol
  10. customdried

Sources & evidence

ORD record
ord-20dfe70612ba4bf2a79bedfcee9a97cc
Source dataset
uspto-grants-2000_04
Patent number
US06048983

Reaction notes

Loading…