N-Methylcyclohexylamine → HCID 18349179, compound

HRID 2268626Notes

Reaction equation

HRID 2268626 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Br:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:18][CH2:19][CH2:20][NH:21][C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)[CH:17]=1)[C:12]([OH:14])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:69][NH:70][CH:71]1[CH2:76][CH2:75][CH2:74][CH2:73][CH2:72]1>CN(C=O)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Br:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:18][CH2:19][CH2:20][NH:21][C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)[CH:17]=1)[C:12]([N:70]([CH:71]1[CH2:76][CH2:75][CH2:74][CH2:73][CH2:72]1)[CH3:69])=[O:14]

Participants

7

Reactant 5

HCID 7514N-MethylcyclohexylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 69950321HCID 69950321, compound

Product 1

HCID 18349179HCID 18349179, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-bromo-5[-2-(pyridin-4-ylamino)-ethoxy]-benzoic acid trifluoroacetate salt (0.034 g), TBTU (0.048 g) and HOBt (0.014 g) in DMF (0.3 ml) was added DIPEA (0.026 ml) followed by N-methylcyclohexylamine (0.020 ml) after 15 min. The reaction mixture was stirred at room temperature for 18 h and then concentrated under reduced pressure. The residue was subjected to preparative hplc and the title compound (0.005 g) was obtained as a colourless gum by concentration of the required fraction under reduced pressure and drying by repetitive addition of acetonitrile and concentration under reduced pressure.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b66875942277416c87212287c627c6f4
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

Loading…