Cesium carbonate → 14-Amino-14-(3-methyl-3h-imidazol-4-yl)-2-oxa-10-aza-tricyclo[13.3.1.13,7]eicosa-1(18),3,5,7(20),15(19),16-hexaene-18-carbonitrile

HRID 413434Notes

Reaction equation

HRID 413434 reaction equation
[NH2:1][C:2]([C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24](F)[CH:23]=1)([C:16]1[N:17]([CH3:21])[CH:18]=[N:19][CH:20]=1)[CH2:3][CH2:4][CH2:5][NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[NH2:1][C:2]1([C:16]2[N:17]([CH3:21])[CH:18]=[N:19][CH:20]=2)[C:22]2=[CH:29][C:28](=[C:25]([C:26]#[N:27])[CH:24]=[CH:23]2)[O:15][C:11]2[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:7][NH:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 185332004-[1-Amino-4-[2-(3-hydroxy-phenyl)-ethylamino]-1-(3-methyl-3H-imidazol-4-yl)-butyl]-2-fluoro-benzonitrile

Product 1

HCID 1020023714-Amino-14-(3-methyl-3h-imidazol-4-yl)-2-oxa-10-aza-tricyclo[13.3.1.13,7]eicosa-1(18),3,5,7(20),15(19),16-hexaene-18-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[1-Amino-4-[2-(3-hydroxy-phenyl)-ethylamino]-1-(3-methyl-3H-imidazol-4-yl)-butyl]-2-fluoro-benzonitrile (0.058 g, 0.142 mmol) was dissolved in DMF (15 mL) and treated with Cs2CO3 (0.324 g, 0.994 mmol). After 18 h at 60° C., the reaction mixture was concentrated in vacuo, dissolved in H2O: 0.1% TFA (3 mL) and purified by RP LC on a Delta PrepPak eluting with 95:5 to 5:95 H2O (0.1% TFA): CH3CN(0.1% TFA) to give the title compound as an 80:20 mixture of enantiomers.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in H2O
  3. custom0.1% TFA (3 mL) and purified by RP LC on a Delta PrepPak
  4. washeluting with 95:5 to 5:95 H2O (0.1% TFA)

Sources & evidence

ORD record
ord-e3be2ab5c3c746e39c481b1d7d0c01ea
Source dataset
uspto-grants-2003_05
Patent number
US06566385B2

Reaction notes

Loading…