Pyridine → HCID 24824243, compound

HRID 1642064Notes

Reaction equation

HRID 1642064 reaction equation
[CH2:1]([O:3][P:4]([C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18])([F:11])[F:10])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].N1C=CC=CC=1.[CH2:25]([O:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:45]=[CH:44][C:43]([C:46](Cl)=[O:47])=[CH:42][CH:41]=2)=[CH:36][CH:35]=1)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].CCOC(C)=O>C(Cl)Cl>[CH2:1]([O:3][P:4]([C:9]([F:11])([F:10])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][C:46]([C:43]1[CH:42]=[CH:41][C:40]([C:37]2[CH:38]=[CH:39][C:34]([O:33][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:35][CH:36]=2)=[CH:45][CH:44]=1)=[O:47])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 110784734-(4-Octyloxyphenyl)benzoyl chlorideHCID 59157971HCID 59157971, compound

Product 1

HCID 24824243HCID 24824243, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tto a solution of [(2-amino-phenyl)-difluoro-methyl]-phosphonic acid diethyl ester NVP-VAV664 in CH2Cl2 are added 5 equivalents of pyridine followed by 1 equivalent of 4′-octyloxy-biphenyl-4-carbonylchloride at rt and the mixture obtained is stirred for ca. 10 to 20 minutes. To the mixture obtained EtOAc is added and and the mixture obtained is extracted with NaHCO3. From the organic phase obtained solvent is evaporated and the evaporation residue is subjected to column chromatography. (Difluoro-{2-[(4′-octyloxy-biphenyl-4-carbonyl)-amino]-phenyl}-methyl)-phosphonic acid diethyl ester is obtained in the form of a colourless powder.

Workup

  1. customthe mixture obtained
  2. additionis added
  3. customthe mixture obtained
  4. extractionis extracted with NaHCO3
  5. customFrom the organic phase obtained solvent
  6. customis evaporated

Sources & evidence

ORD record
ord-fde220976dca4783812cca1573bbbbf1
Source dataset
uspto-grants-2012_02
Patent number
US08119617B2

Reaction notes

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