1-Hydroxybenzotriazole → HCID 18349095, compound

HRID 2268627Notes

Reaction equation

HRID 2268627 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=[N:43][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42]C1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH:50]1[CH:51]=CC2N(O)N=NC=2[CH:55]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:51]([N:43]([CH:38]1[CH2:39][CH2:40][CH2:41][CH2:42]1)[C:12](=[O:14])[C:11]1[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]=[C:9]([Br:8])[CH:10]=1)[CH:50]=[CH2:55]

Participants

6

Reactant 4

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

Product 1

HCID 18349095HCID 18349095, compoundYield 52.3%

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-allylcyclopentyamine (0.022 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 (0.022 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-a46217a79ffc422a870fefd3b73d0c2e
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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