Tetrahydrofuran → HCID 178493481, compound

HRID 630400Notes

Reaction equation

HRID 630400 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([Cl:12])=[CH:10][C:9]([CH2:13][OH:14])=[C:8]([O:15][CH3:16])[CH:7]=1.[OH:17][C:18]([C:35]1[S:36][CH:37]=[CH:38][CH:39]=1)([C:30]1[S:31][CH:32]=[CH:33][CH:34]=1)[C:19]([O:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([NH:28][CH3:29])[CH2:24][CH2:23]1)=[O:20].C(N(CC)CC)C.C1COCC1>C(#N)C>[OH:17][C:18]([C:30]1[S:31][CH:32]=[CH:33][CH:34]=1)([C:35]1[S:36][CH:37]=[CH:38][CH:39]=1)[C:19]([O:21][C@H:22]1[CH2:23][CH2:24][C@H:25]([N:28]([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:7]=[C:8]([O:15][CH3:16])[C:9]([CH2:13][OH:14])=[CH:10][C:11]=2[Cl:12])[CH3:29])[CH2:26][CH2:27]1)=[O:20]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 67145252[4-(3-Bromopropoxy)-5-chloro-2-methoxyphenyl]methanol2×HCID 178484861HCID 178484861, compound3×

Product 1

HCID 178493481HCID 178493481, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of [4-(3-bromopropoxy)-5-chloro-2-methoxyphenyl]methanol (intermediate 55; 386 mg; 1.25 mmol), trans-4-(methylamino)cyclohexyl hydroxy(di-2-thienyl)acetate (intermediate 5; 438 mg, 1.25 mmol) and triethylamine 0.345 ml; 2.49 mmol) in 12 ml acetonitrile and 8.7 ml THF was stirred at 70° C. for 16 hr. An additional amount of intermediate 5 (219 mg; 0.62% mmol) was added and the heating prosecuted for 24 hr. The solvent was evaporated in vacuum and the residue purified by preparative reversed-phase HPLC (hexane/EtOAc from 0 to 40%), affording the title compound (80%) as a light yellow oil.

Workup

  1. customThe solvent was evaporated in vacuum
  2. customthe residue purified by preparative reversed-phase HPLC (hexane/EtOAc from 0 to 40%)

Sources & evidence

ORD record
ord-f505b2689fa24e6fa0defedf6066f48c
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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