2-(Methylamino)ethanol → 6-{4-[4-(4-Fluoro-benzyl)-phthalazin-1-yl]-piperazin-1-yl}-N-(2-hydroxyethyl)-N-methyl-nicotinamide

HRID 42210Notes

Reaction equation

HRID 42210 reaction equation
[F:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([N:17]3[CH2:22][CH2:21][N:20]([C:23]4[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][N:24]=4)[CH2:19][CH2:18]3)=[N:9][N:8]=2)=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:67][NH:68][CH2:69][CH2:70][OH:71]>CN(C=O)C>[F:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([N:17]3[CH2:18][CH2:19][N:20]([C:23]4[CH:31]=[CH:30][C:26]([C:27]([N:68]([CH2:69][CH2:70][OH:71])[CH3:67])=[O:28])=[CH:25][N:24]=4)[CH2:21][CH2:22]3)=[N:9][N:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 80162-(Methylamino)ethanolHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 592406356-{4-[4-(4-Fluoro-benzyl)-phthalazin-1-yl]-piperazin-1-yl}-nicotinic acid

Product 1

HCID 592406256-{4-[4-(4-Fluoro-benzyl)-phthalazin-1-yl]-piperazin-1-yl}-N-(2-hydroxyethyl)-N-methyl-nicotinamideYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-{4-[4-(4-Fluoro-benzyl)-phthalazin-1-yl]-piperazin-1-yl}-nicotinic acid (100 mg, 0.225 mmol), DMF (0.5 mL), Diisopropylethylamine (195 μL, 1.125 mmol), HBTU (102 mg, 0.270 mmol), and 2-(methylamino)ethanol (18 μL, 0.225 mmol) are combined in a 10 mL flask and stirred for 4 h at room temperature. Concentrate to remove DMF in vacuo. The residue is purified by flash chromatography on silica gel (0-25% MeOH/CH2Cl2 with 5% TEA) to afford the title compound (68.2 mg, 61%).

Workup

  1. concentrationConcentrate
  2. customto remove DMF in vacuo
  3. customThe residue is purified by flash chromatography on silica gel (0-25% MeOH/CH2Cl2 with 5% TEA)

Sources & evidence

ORD record
ord-e061af082f1a4af0bee37570ed4744d8
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Reaction notes

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