HCID 11049334, compound → Pranlukast

HRID 1108868Notes

Reaction equation

HRID 1108868 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]=[C:8]1[C:13]2[CH:14]=[CH:15][CH:16]=[C:17]([NH:18][C:19](=[O:37])[C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:22][CH:21]=3)[C:12]=2[O:11][C:10]([C:38]2[N:39]=[N:40][N:41](O)[N:42]=2)=[CH:9]1>O1CCCC1.[Ti](Cl)(Cl)(Cl)Cl.[Ti]>[CH:34]1[CH:35]=[CH:36][C:31]([CH2:30][CH2:29][CH2:28][CH2:27][O:26][C:23]2[CH:24]=[CH:25][C:20]([C:19]([NH:18][C:17]3[CH:16]=[CH:15][CH:14]=[C:13]4[C:8](=[O:7])[CH:9]=[C:10]([C:38]5[N:42]=[N:41][NH:40][N:39]=5)[O:11][C:12]=34)=[O:37])=[CH:21][CH:22]=2)=[CH:32][CH:33]=1

Participants

6

Reactant 2

HCID 11049334HCID 11049334, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 4887Pranlukast

Reagents, catalysts & solvents 3

HCID 23963TitaniumCatalystHCID 24193Titanium TetrachlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of titanium tetrachloride (0.49 ml, 1.8 mole equivalents) in tetrahydrofuran (2.5 ml) was added lithium aluminium hydride (123 mg, 1.3 mole equivalents) to produce a black suspension of titanium (0) which was stirred for 15 minutes. 4-Oxo-8-[4-(4-phenylbutoxy)benzoylamino]-2-(2-hydroxytetrazol-5-yl)-4H-1-benzopyran (1.24, 1 mole equivalent) was added, together with additional tetrahydrofuran (5 ml). The mixture was stirred for 60 minutes at room temperature and then heated at reflux for 90 minutes to give pranlukast in 71% solution yield.

Workup

  1. customto produce
  2. stirringThe mixture was stirred for 60 minutes at room temperature
  3. temperatureheated
  4. temperatureat reflux for 90 minutes

Sources & evidence

ORD record
ord-aca7cc5aef1f4571a4e6fdbc3abf17e5
Source dataset
uspto-grants-2000_05
Patent number
US06069257

Reaction notes

Loading…