Dabco → HCID 24823497, compound

HRID 1642065Notes

Reaction equation

HRID 1642065 reaction equation
[CH2:1]([O:3][P:4]([C:9]([F:42])([F:41])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]([CH3:40])[C:17]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[CH:27][CH:26]=3)=[CH:21][CH:20]=2)=[O:18])[CH:11]=1)(=[O:8])[O:5]CC)[CH3:2].C1N2CCN(CC2)C1>C(#N)C>[CH2:1]([O:3][P:4]([C:9]([F:42])([F:41])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]([CH3:40])[C:17]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:26]=[CH:27][C:28]([O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[CH:29][CH:30]=3)=[CH:21][CH:20]=2)=[O:18])[CH:11]=1)(=[O:5])[OH:8])[CH3:2]

Participants

4

Reactant 2

HCID 9237DabcoHCID 24823495HCID 24823495, compound

Product 1

HCID 24823497HCID 24823497, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (difluoro-{3-[methyl-(4′-octyloxy-biphenyl-4-carbonyl)-amino]-phenyl}-methyl)-phosphonic acid diethyl ester (compound of example 59 in TABLE 2 below) and aproximately 3 to 5 equivalents of DABCO in acetonitrile solution is heated to 150° C. in a microwave reactor for less then 40 minutes. The mixture obtained is partitioned between EtOAc and 1N aqueous HCl. From the mixture obtained the organic phase is separated, washed with 1N aqueous HCl, and evaporated to dryness. (Difluoro-{3-[methyl-(4′-octyloxy-biphenyl-4-carbonyl)-amino]-phenyl}-methyl)-phosphonic acid monoethyl ester is obtained.

Workup

  1. customThe mixture obtained
  2. customis partitioned between EtOAc and 1N aqueous HCl
  3. customFrom the mixture obtained the organic phase
  4. customis separated
  5. washwashed with 1N aqueous HCl
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-98a3fe1f25b546378fd9260f4690dfa1
Source dataset
uspto-grants-2012_02
Patent number
US08119617B2

Reaction notes

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