Dimethylamine → HCID 68765372, compound

HRID 1170933Notes

Reaction equation

HRID 1170933 reaction equation
C[O:2][C:3](=O)[CH:4]([NH:11][CH:12]([C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[OH:32])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-].[Na+].[CH3:36][N:37](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)[CH3:38].[B-](F)(F)(F)F.CNC>C(O)C>[CH3:24][O:23][C:17]1[CH:16]=[C:15]([CH2:14][CH2:13][CH:12]([NH:11][CH:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:3]([N:37]([CH3:38])[CH3:36])=[O:2])[C:25]2[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=2[OH:32])[CH:20]=[CH:19][C:18]=1[O:21][CH3:22]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 14798Sodium HydroxideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59553847HCID 59553847, compound

Product 1

HCID 68765372HCID 68765372, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 36.2 mg (0.8 mmol) [3-(3,4-dimethoxy-phenyl)-1-(5-fluoro-2-hydroxy-phenyl)-propylamino]-phenyl-acetic acid methyl ester and 0.32 mmol NaOH aq. in ethanol was evaporated to dryness and dissolved in DMF. TBTU (0.24 mmol) and dimethylamine (0.24 mmol) was added and the mixture was stirred for 1 h at room temperature. The mixtures was evaporated and purified by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid. The product containing fractions were evaporated to yield 9.8 mg (26%) of the title compound. MS (m/e): 467.2 (MH+).

Workup

  1. customwas evaporated to dryness
  2. dissolutiondissolved in DMF
  3. customThe mixtures was evaporated
  4. custompurified by preparative HPLC on reversed phase
  5. washeluting with a gradient
  6. customformed from acetonitrile, water and formic acid
  7. additionThe product containing fractions
  8. customwere evaporated

Sources & evidence

ORD record
ord-3985bca5e24a4764ab90c187ac3ccddd
Source dataset
uspto-grants-2010_11
Patent number
US07829563B2

Reaction notes

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